N-bromobutanimide → N-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide

HRID 2196646Notes

Reaction equation

HRID 2196646 reaction equation
[F:1][C:2]1[C:19]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])=[CH:18][CH:17]=[C:16]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:5].[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:28][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:16]([F:27])=[CH:17][CH:18]=[C:19]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[C:2]=3[F:1])[CH:8]=2)[NH:13][CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 441994082,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

Product 1

HCID 44223912N-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2,6-Difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.500 g, 1.268 mmol) was charged to a 100 mL round-bottom flask. CHCl3 (25 mL) was added to form a slurry. N-Bromosuccinimide (0.271 g, 1.52 mmol) was added and stirred for 20 minutes. The reaction mixture was filtered, washed with DCM, and dried under vacuum providing N-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.427 g, 71.2%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 12.12 (br s, 1H), 11.04 (s, 1H), 9.81 (br s, 1H), 8.41-8.43 (m, 1H), 8.34-8.35 (m, 1H), 7.74-7.76 (m, 1H), 7.53-7.59 (m, 1H), 7.25-7.30 (m, 1H), 3.11-3.15 (m, 2H), 1.75-1.80 (m, 2H), 0.98-1.02 (m, 3H); m/z (APCI-pos) M+1=473.0, 475.0.

Workup

  1. customto form a slurry
  2. filtrationThe reaction mixture was filtered
  3. washwashed with DCM
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ccb1c5d9a4824a1d95e0db4da22b59ea
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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