5-Iodo-1H-pyrrolo[2,3-b]pyridine → Propane-1-sulfonic acid [2-fluoro-3-(5-iodo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-phenyl]-amide

HRID 217619Notes

Reaction equation

HRID 217619 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:11][C:12]1[C:17]([CH:18]=[O:19])=[C:16](F)[CH:15]=[CH:14][C:13]=1[NH:21][S:22]([CH2:25][CH:26](C)[CH3:27])(=[O:24])=[O:23].FC1C(C=O)=CC=CC=1NS(CCC)(=O)=O>>[F:11][C:12]1[C:17]([C:18]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([I:1])[CH:3]=3)[NH:8][CH:9]=2)=[O:19])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23]

Participants

4

Reactant 3

HCID 242292145-Iodo-1H-pyrrolo[2,3-b]pyridineHCID 58086814Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amideHCID 583169302-Methyl-propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide

Product 1

HCID 59569593Propane-1-sulfonic acid [2-fluoro-3-(5-iodo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-phenyl]-amide

Procedure

was prepared similarly to the protocol of Scheme 10, replacing 5-bromo-1H-pyrrolo[2,3-b]pyridine 55 with 5-iodo-1H-pyrrolo[2,3-b]pyridine 24 and 2-methyl-propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide 59 with propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide 67 in step 1.

Workup

  1. customwas prepared similarly to the protocol of Scheme 10

Sources & evidence

ORD record
ord-81c39a3099874acdb57423d1da47f238
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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