Chloroform → HCID 44223336, compound

HRID 2196664Notes

Reaction equation

HRID 2196664 reaction equation
BrN1C(=O)CCC1=O.CN(C=O)C.[Cl:14][C:15]1[CH:16]=[C:17]([C:21]2[NH:47][C:24]3=[N:25][CH:26]=[C:27]([NH:29][C:30](=[O:46])[C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([NH:38][S:39]([CH2:42][CH2:43][CH3:44])(=[O:41])=[O:40])[C:32]=4[F:45])[CH:28]=[C:23]3[CH:22]=2)[CH:18]=[CH:19][CH:20]=1.FC1C(NS(CCC)(=O)=O)=CC=C(F)C=1C(NC1C=C2C=C(C3C=CC=CC=3)NC2=NC=1)=O.C(Cl)(Cl)[Cl:82]>>[Cl:82][C:22]1[C:23]2[C:24](=[N:25][CH:26]=[C:27]([NH:29][C:30](=[O:46])[C:31]3[C:36]([F:37])=[CH:35][CH:34]=[C:33]([NH:38][S:39]([CH2:42][CH2:43][CH3:44])(=[O:40])=[O:41])[C:32]=3[F:45])[CH:28]=2)[NH:47][C:21]=1[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=1

Participants

6

Reactant 5

HCID 6212ChloroformHCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 44223627HCID 44223627, compoundHCID 44223676HCID 44223676, compound

Product 1

HCID 44223336HCID 44223336, compoundYield 38%

Procedure

N-(3-chloro-2-(3-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (38%) was prepared according to Example 25, substituting N-chlorosuccinimide for N-bromosuccinimide, DMF for CHCl3, and N-(2-(3-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide for 2,6-difluoro-N-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide. 1H NMR (400 MHz, DMSO-d6) δ 12.55 (s, 1H), 11.11 (s, 1H), 9.82 (s, 1H), 8.49-8.46 (m, 2H), 8.01-7.99 (m, 1H), 7.96-7.93 (m, 1H), 7.63-7.52 (m, 3H), 7.32-7.26 (m, 1H), 3.16-3.11 (m, 2H), 1.82-1.74 (m, 2H), 1.03-0.98 (m, 3H); m/z (APCI-pos) M+1=539.0.

Sources & evidence

ORD record
ord-487f3250fc0141c7a8e588874bb903cd
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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