Methanol → N-[5-Chloro-2-(1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-pyridin-3-yl]-3-fluoro-4-methyl-benzenesulfonamide

HRID 1898288Notes

Reaction equation

HRID 1898288 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[NH:17][CH:18]=[CH:19][C:12]=23)=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:20][C:21]1[CH:22]=[C:23]([S:28](Cl)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[CH3:27].CO.[OH-].[Na+]>N1C=CC=CC=1.O>[Cl:8][C:6]1[CH:7]=[C:2]([NH:1][S:28]([C:23]2[CH:24]=[CH:25][C:26]([CH3:27])=[C:21]([F:20])[CH:22]=2)(=[O:29])=[O:30])[C:3]([C:9]([C:11]2[C:12]3[CH:19]=[CH:18][NH:17][C:13]=3[N:14]=[CH:15][CH:16]=2)=[O:10])=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 27786003-Fluoro-4-methylbenzene-1-sulfonyl chlorideHCID 58268254(3-Amino-5-chloro-pyridin-2-yl)-(1H-pyrrolo[2,3-b]pyridin-4-yl)-methanone

Product 1

HCID 44176725N-[5-Chloro-2-(1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-pyridin-3-yl]-3-fluoro-4-methyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Prepared from 18 mg (0.066 mmol) of (3-amino-5-chloro-pyridin-2-yl)-(1H-pyrrolo[2,3-b]pyridin-4-yl)-methanone and 48 mg (0.25 mmol) of 3-fluoro-4-methyl-benzenesulfonyl chloride in 0.10 mL pyridine using procedure x. After the sulfonylation was complete, 2 mL methanol, 0.5 mL water and 32 mg sodium hydroxide were used. Yield: 20 mg of a yellow solid. LC-MSD, m/z for C20H14ClFN4O3S [M+H]+=445.0, 447.0.

Sources & evidence

ORD record
ord-c4bc7457cd4c4b559e4377b41cf5a751
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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