5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one → HCID 25114697, compound

HRID 2191439Notes

Reaction equation

HRID 2191439 reaction equation
[CH3:1][C:2]1[C:6]2[C:7](=[O:20])[N:8]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][C:3]=1[CH:21]=O.[Br:23][C:24]1[CH:25]=[C:26]2[CH2:32][C:31](=[O:33])[NH:30][C:27]2=[N:28][CH:29]=1>>[Br:23][C:24]1[CH:25]=[C:26]2[C:27]([NH:30][C:31](=[O:33])/[C:32]/2=[CH:21]\[C:3]2[NH:4][C:5]3[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:7](=[O:20])[C:6]=3[C:2]=2[CH3:1])=[N:28][CH:29]=1

Participants

3

Reactant 2

HCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-oneHCID 592500683-Methyl-5-(2-morpholin-4-yl-ethyl)-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 25114697HCID 25114697, compoundYield 60%

Procedure

The title compound was prepared under the same conditions as described in step 4 of Example 10 with 3-methyl-5-(2-morpholin-4-yl-ethyl)-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 10c obtained from step 3 of Example 10 and 5-bromo-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as starting materials to obtain (Z)-2-(5-bromo-2-oxo-1,2-dihydro-pyrrolo[2,3-b]pyrid in-3-ylidenemethyl)-3-methyl-5-(2-morpholin-4-yl-ethyl)-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-c]azepin-4-one 22 (59 mg, yield 60%) as an orange solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-6dd687621d134c698e761eb4e42fd989
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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