6-Phenoxypyridine-3-sulphonyl chloride → 5-Ethyl-2-fluoro-4-{3-[5-(6-phenoxy-pyridine-3-sulfonyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-6-yl}-phenol

HRID 340014Notes

Reaction equation

HRID 340014 reaction equation
Br.Br.Br.[CH2:4]([C:6]1[C:7]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([C:23]4[NH:24][C:25]5[CH2:30][CH2:29][NH:28][CH2:27][C:26]=5[N:31]=4)=[N:19][NH:20]3)=[CH:16][CH:15]=2)=[CH:8][C:9]([F:13])=[C:10]([OH:12])[CH:11]=1)[CH3:5].[O:32]([C:39]1[N:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:4]([C:6]1[C:7]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([C:23]4[NH:24][C:25]5[CH2:30][CH2:29][N:28]([S:45]([C:42]6[CH:43]=[N:44][C:39]([O:32][C:33]7[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=7)=[CH:40][CH:41]=6)(=[O:46])=[O:47])[CH2:27][C:26]=5[N:31]=4)=[N:19][NH:20]3)=[CH:16][CH:15]=2)=[CH:8][C:9]([F:13])=[C:10]([OH:12])[CH:11]=1)[CH3:5]

Participants

3

Reactant 2

HCID 27764996-Phenoxypyridine-3-sulphonyl chlorideHCID 1784192405-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazol[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt

Product 1

HCID 1784369405-Ethyl-2-fluoro-4-{3-[5-(6-phenoxy-pyridine-3-sulfonyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-6-yl}-phenolYield 17.2%

Procedure

The title compound was prepared from 5-ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt (Preparation 25, 50 mg, 80 μmol) and 6-phenoxy-pyridine-3-sulfonyl chloride (22 mg, 80 μmol) using the method of Example 6. The crude material was purified by HPLC Method A to afford 8.4 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method A

Sources & evidence

ORD record
ord-bb3ba311e2a64d009194f5a37857984f
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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