3-Chloro-4-(3-fluorobenzyloxy)aniline → tert-Butyl 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

HRID 38568

Reaction equation

HRID 38568 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)[NH2:5].Cl[C:19]1[C:24]([C:25]#[N:26])=[CH:23][N:22]=[C:21]2[S:27][C:28]3[CH2:29][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31][CH2:32][C:33]=3[C:20]=12>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:19]2[C:24]([C:25]#[N:26])=[CH:23][N:22]=[C:21]3[S:27][C:28]4[CH2:29][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31][CH2:32][C:33]=4[C:20]=23)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1

Participants

3

Reactant 2

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 58116935tert-Butyl 4-chloro-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Product 1

HCID 58116968tert-Butyl 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Procedure

In analogy to Example 54A, the title compound was synthesized from 3-chloro-4-[(3-fluorobenzyl)oxy]aniline from Example 4A (180 mg, 0.72 mmol) and tert-butyl 4-chloro-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c′]dipyridine-7(6H)-carboxylate (250 mg, 0.72 mmol) from Example 53A to yield 258 mg (64%).

Workup

  1. customto yield 258 mg (64%)

Sources & evidence

ORD record
ord-3bb2cc15702a4fe494510c75cdb9083c
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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