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23
Preparation of
19 (Step a)
To a suspension of JandaJelTM-OH
(2.00 g, 1.0 mmol/g, 2.0 mmol) in anhyd DMF (13 mL) were
added 6-heptynoic acid (0.76 mL, 6.0 mmol), pyridine (0.65 mL, 8.0
mmol), and 2,6-dichlorobenzoyl chloride (0.86 mL, 6.0 mmol). The mixture
was agitated at r.t. for 12 h. The resin was washed alternately
with DMF and H2O (3×), CHCl3 and
MeOH (3×), and Et2O, and then dried under vacuum
to yield 19 (2.13 g).
Preparation of 20 (Step b)
To
a suspension of 19 (2.0 mmol), 4b (2.55 g, 5.0 mmol), PdCl2(PPh3)2 (140
mg, 0.20 mmol), and CuI (76.2 mg, 0.40 mmol) in anhyd DMF (16 mL)
was added Et3N (5.3 mL, 38 mmol) at r.t. under argon.
The mixture was agitated at r.t. for 12 h. The resin was washed
alternately with DMF and H2O (3×), CHCl3 and
MeOH (3×), and Et2O, and then dried under vacuum
to yield 20 (2.68 g).
Preparation of 21 (Step c)
To
a suspension of 20 (2.0 mmol) in anhyd
DMF (22 mL) was added Br3P (0.95 mL, 10 mmol) at r.t.
under argon. The mixture was agitated at r.t. for 6 h. The resin
was washed alternately with DMF and H2O (3×),
CHCl3 and MeOH (3×), and Et2O, and
then dried under vacuum to yield 21 (2.66
g, 0.46 mmol/g calculated by increased resin weight).
General Procedure for N-Alkylation (Step d)
To
a solution of 5b-g (3.9
mmol) in DME (5.2 mL) and DMF (1.3 mL) was added t-BuOLi
(3.6 mmol) under argon. The mixture was agitated at r.t. for 30
min, after which 21 (0.80 g, 0.37 mmol)
was added. The mixture was then agitated at r.t. for 24 h. The resin
was washed alternately with DMF and H2O (3×),
CHCl3 and MeOH (3×), and Et2O, and
then dried under vacuum to yield N-alkylation products.
General Procedure for Heck Reaction (Step e)
To
a test tube containing the N-alkylation product (0.045 mmol), Pd(OAc)2 (0.032
mmol), Ph3P (0.064 mmol), and KOAc (0.64 mmol) was added
benzonitrile (0.8 mL) under argon. The mixture was agitated at 80 ˚C
for 12 h. The resin was washed alternately with DMF and H2O
(3×), CHCl3 and MeOH (3×), and Et2O,
and then dried under vacuum to yield 22.
General Procedure for Methylation of 22 (Step
f)
To a test tube containing 22 (0.041
mmol), MeB(OH)2 (0.45 mmol), Pd(OAc)2 (0.027
mmol), S-Phos (0.054 mmol), and K3PO4×nH2O
(0.45 mmol) was added toluene (0.8 mL) under argon. The mixture
was agitated at 100 ˚C for 12 h. The resin was washed alternately
with DMF and H2O (3×), CHCl3 and MeOH
(3×), and Et2O, and then dried under vacuum.
General Procedure for Arylation of 22 (Step
g)
To a test tube containing 22 (0.041
mmol), p-Ac-C6H4B(OH)2 (0.45
mmol), Pd(OAc)2 (0.027 mmol), S-Phos (0.054 mmol), and
K3PO4 (0.45 mmol) was added toluene (0.8 mL)
under argon. The mixture was agitated at 100 ˚C for 12
h. The resin was washed alternately with DMF and H2O
(3×), CHCl3 and MeOH (3×), and Et2O,
and then dried under vacuum.
General
Procedure for Amination of 22 (Step h)
To a test tube
containing 22 (0.041 mmol), BnNH2 (0.46 mmol),
Pd(OAc)2 (0.066 mmol), XANTPHOS (0.073 mmol), and K2CO3 (0.46
mmol) was added 1,4-dioxane (0.8 mL) under argon. The mixture was
agitated at 100 ˚C for 12 h. The resin was washed alternately
with DMF and H2O (3×), CHCl3 and
MeOH (3×), and Et2O, and then dried under vacuum.
General Procedure for NaBH
4
Reduction of
22 (Step i)
To a suspension of 22 (0.021
mmol) in THF-EtOH (3:1, 0.5 mL) was added NaBH4 (0.11
mmol) under argon. The mixture was agitated at r.t. for 3 h. The
resin was washed alternately with DMF and H2O (3×),
CHCl3 and MeOH (3×), and Et2O, and
then dried under vacuum to yield 23.
General Procedure for Reductive Cleavage (Step
j)
To a test tube containing 23 or 24 (0.021 mmol), Pd(OAc)2 (0.0084
mmol), and dppp (0.0092 mmol) were added anhyd 1,4-dioxane (0.5
mL), Et3N (0.63 mmol), and formic acid (0.63 mmol) under
argon. The mixture was agitated at
100 ˚C for
12 h. The mixture was filtered and thoroughly washed with CHCl3.
The filtrate was concentrated in vacuo and the residue was purified
by PLC eluting with 6% MeOH-CHCl3 to
yield 25 or 26.
Spectral data of 25bA agreed with the reported
ones.
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