N-bromobutanimide → HCID 44223335, compound

HRID 2196663Notes

Reaction equation

HRID 2196663 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:33]([NH:34][S:35]([CH2:38][CH2:39][CH3:40])(=[O:37])=[O:36])=[CH:32][CH:31]=[C:30]([F:41])[C:11]=1[C:12]([NH:14][C:15]1[CH:16]=[C:17]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:21][C:18]2=[N:19][CH:20]=1)=[O:13]>C(Cl)(Cl)Cl>[Br:1][C:23]1[C:17]2[C:18](=[N:19][CH:20]=[C:15]([NH:14][C:12](=[O:13])[C:11]3[C:30]([F:41])=[CH:31][CH:32]=[C:33]([NH:34][S:35]([CH2:38][CH2:39][CH3:40])(=[O:37])=[O:36])[C:10]=3[F:9])[CH:16]=2)[NH:21][C:22]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 44223627HCID 44223627, compound

Product 1

HCID 44223335HCID 44223335, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (1.1 eq.) was added to a slurry of 2,6-difluoro-N-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (11 mg, 1.0 eq.) in CHCl3 (1.0 mL), and the reaction mixture stirred at ambient temperature for 16 hours. The reaction mixture was filtered, and the solids were washed with CH2Cl2. The resulting solids were then purified by silica gel chromatography (eluting with 5% MeOH/CH2Cl2) to afford N-(3-bromo-2-phenyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide as a solid (9 mg, 69%). 1H NMR (400 MHz, DMSO-d6) δ 12.53 (s, 1H), 11.08 (s, 1H), 9.82 (s, 1H), 8.47-8.44 (m, 1H), 8.39-8.37 (m, 1H), 7.95-7.91 (m, 2H), 7.61-7.53 (m, 3H), 7.51-7.45 (m, 1H), 7.32-7.26 (m, 1H), 3.16-3.11 (m, 2H), 1.83-1.74 (m, 2H), 1.03-0.98 (m, 3H); m/z (APCI-neg) M−1=549.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with CH2Cl2
  3. customThe resulting solids were then purified by silica gel chromatography (eluting with 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-687cd4bcb0594dae92ab0959354b28e4
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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