Ethyl 4-oxocyclohexanecarboxylate → 4-[3-Ethyl-1-(4-fluorophenyl)-1H-indazole-6-yl]4-hydroxy-cyclohexanecarboxylic acid ethyl ester

HRID 322101Notes

Reaction equation

HRID 322101 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][CH3:19])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]1)=[O:24])[CH3:21]>C(OCC)(=O)C>[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][C:28]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([CH2:18][CH3:19])=[N:7][N:8]3[C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[CH:4][CH:3]=2)([OH:31])[CH2:27][CH2:26]1)=[O:24])[CH3:21]

Participants

4

Reactant 2

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 98184726-Bromo-3-ethyl-1-(4-fluorophenyl)-1H-indazole

Product 1

HCID 99533734-[3-Ethyl-1-(4-fluorophenyl)-1H-indazole-6-yl]4-hydroxy-cyclohexanecarboxylic acid ethyl esterYield 56.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared according to the method described in Example 6 of U.S. Ser. No. 09/308,954, filed May 8, 1997 as Attorney Docket No. PC9798, starting with 3.0 grams (9.4 mmol) of 6-bromo-3-ethyl-1-(4-fluoro-phenyl)-1H-indazole and 2.0 grams (11.7 mmol) of 4-oxo-cyclohexanecarboxylic acid ethyl ester to give after silica gel flash column chromatography (using 20% ethyl acetate 80% hexane as elutant) 2.17 grams of light yellow semi-solid which was a mixture of diastereoisomers. 1H NMR (400 MHz, CDCl3) δ 1.25-1.3 (t, 3H); 1.4-1.5 (t, 3H); 1.6-1.78 (m, 2H); 1.8-2.5 (m, 7H); 2.70 (m, 1H); 3.04 (m, 2H); 4.16 (m, 2H); 7.17-7.28 (m, 3H); 7.61-7.79 (m, 4H); MS, m/z 324.4 (M+H+, base).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-158dbbd98d824286b877c7eb3bcef6fc
Source dataset
uspto-grants-2001_04
Patent number
US06211222B1

Reaction notes

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