Water → [5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanol

HRID 1862460Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:16]([CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:15]([S:24][C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)[N:14]([CH:33]([CH3:35])[CH3:34])[N:13]=1)=O)C.O.[OH-].[Na+]>O1CCCC1>[Cl:32][C:27]1[CH:26]=[C:25]([S:24][C:15]2[N:14]([CH:33]([CH3:35])[CH3:34])[N:13]=[C:12]([CH2:10][OH:9])[C:16]=2[CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH:30]=[C:29]([Cl:31])[CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution containing 0.4 ml of lithium aluminium hydride (1M solution in THF) in 2 ml of anhydrous tetrahydrofuran at 0° C. under nitrogen was treated dropwise with a solution of 154 mg of 5-(3,5-Dichloro-phenylsulfanyl)-1-isopropyl-4-pyridin-4-ylmethyl-1H-pyrazole-3-carboxylic acid ethyl ester in 2 ml of anhydrous tetrahydrofuran. The mixture was stirred at 0° C. for 0.5 h then treated with 0.012 ml of water, 0.012 ml of 2N sodium hydroxide solution and then 0.018 ml of water. The mixture was stirred for 0.5 h at 0° C.; the mixture was filtered and then the solvent removed. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (1:19) for the elution to give 90 mg of 5-(3,5dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H -pyrazole-3-methanol as a white gum. Mass spectrum (ESI) m/z 408 [M+H]+. 1H NMR (DMSO) 1.30 (d, 6H), 3.90 (s, 2H), 4.55 (d, 2H), 4.72 (m, 1H), 5.30 (t, 1H), 6.85 (s, 2H), 7.15 (d, 2H), 7.35 (s, 1H), 8.30 (d, 2H).

Workup

stirringThe mixture was stirred for 0.5 h at 0° C.
filtrationthe mixture was filtered
customthe solvent removed
customThe residue was purified by flash chromatography on silica gel
washfor the elution

Sources & evidence

ORD record: ord-e14263741d104f8487ad4a0af3c6b378
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538015B1

Reaction notes

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