4-Bromo-3-methylaniline → N-(4-bromo-3-methylphenyl)3-[(1H-Pyrrolo[2,3-b]pyridin-3-ylmethyl)amino]thiophene-2-carboxamide

HRID 641794Notes

Reaction equation

HRID 641794 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[NH2:16])=[O:10])=[CH:4][C:3]=1[CH3:17].BrC1C=CC(N)=CC=1C.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][N:34]=2)[C:29]([CH:36]=O)=[CH:28]1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[NH:16][CH2:36][C:29]2[C:30]3[C:35](=[N:34][CH:33]=[CH:32][CH:31]=3)[NH:27][CH:28]=2)=[O:10])=[CH:4][C:3]=1[CH3:17]

Participants

4

Reactant 3

HCID 233594-Bromo-3-methylanilineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 61091031N-(4-bromo-3-methylphenyl)3-aminothiophene-2-carboxamide

Product 1

HCID 10252733N-(4-bromo-3-methylphenyl)3-[(1H-Pyrrolo[2,3-b]pyridin-3-ylmethyl)amino]thiophene-2-carboxamide

Procedure

EXAMPLE 9 was prepared according to the procedure described in EXAMPLE 5 using N-(4-bromo-3-methylphenyl)3-aminothiophene-2-carboxamide (prepared as described in EXAMPLE 1, part 1, using 4-bromo-3-methylaniline instead of 4-trifluoromethoxyaniline) and 7-azaindole-3-carboxaldehyde (EXAMPLE 8, part 1) instead of 2-(N-methylcarbamoyl)pyridine-4-carboxaldehyde. MS (ES+): 441, 443 [MH+]

Workup

  1. customEXAMPLE 9 was prepared
  2. customprepared

Sources & evidence

ORD record
ord-05e48d04eef4445183965ca82c93aac5
Source dataset
uspto-grants-2010_04
Patent number
US07696225B2

Reaction notes

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