Methanol → (2-{[1-(3-Chlorobenzyl)-5-fluoro-3-(1-naphthylsulfonyl)-1H-indazol-7-yl]oxy}ethyl)amine

HRID 2240061Notes

Reaction equation

HRID 2240061 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([F:37])[CH:10]=[C:11]2[C:15]=1[N:14]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[N:13]=[C:12]2[S:24]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[N+]=[N-].CO>C1COCC1.[Pd]>[Cl:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:14]1[C:15]2[C:11](=[CH:10][C:9]([F:37])=[CH:8][C:7]=2[O:6][CH2:5][CH2:4][NH2:1])[C:12]([S:24]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)(=[O:25])=[O:26])=[N:13]1

Participants

5

Reactant 2

HCID 887MethanolHCID 866107637-(2-Azido-ethoxy)-1-(3-chloro-benzyl)-5-fluoro-3-(naphthalene-1-sulfonyl)-1H-indazole

Product 1

HCID 58812152(2-{[1-(3-Chlorobenzyl)-5-fluoro-3-(1-naphthylsulfonyl)-1H-indazol-7-yl]oxy}ethyl)amineYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-(2-azido-ethoxy)-1-(3-chloro-benzyl)-5-fluoro-3-(naphthalene-1-sulfonyl)-1H-indazole (0.09 g, 0.17 mmoles) and 10% Pd/C in THF (5 mL), and methanol (15 mL) was hydrogenated in a Parr hydrogenation bottle (250 mL) at 52 Ib/in2 for 2 hours. The mixture was filtered through Celite, and the filtrate was concentrated under vacuum. The crude product was purified by flash chromatography using as eluent 5% CH3OH/CH2Cl2 to afford the title compound as an off-white solid (0.08 g, 0.14 mmoles), MS: (ES+) 511 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fd90b5841c8943839d7d0a0d572db88a
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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