Lithium Hydroxide → HCID 67361802, compound

HRID 1183175Notes

Reaction equation

COC(C1C=C(O)N(C2C=CC=CC=2F)N=1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC1C=CC=CC=1C#N.C[O:35][C:36]([C:38]1[CH:42]=[C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]#[N:52])[N:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[N:39]=1)=[O:37].[OH-].[Li+]>CN(C=O)C.C1COCC1.O>[C:51]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[CH2:44][O:43][C:41]1[N:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[N:39]=[C:38]([C:36]([OH:37])=[O:35])[CH:42]=1)#[N:52]

Participants

Conditions

Temperature: 60 °C

Procedure

1-(2-Fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid methyl ester (200 mg, 0.847 mmol) were dissolved in 5 ml of DMF and cesium carbonate (552 mg, 1.7 mmol) and 2-bromomethyl-benzonitrile (166 mg, 0.85 mmol) were added. The mixture was stirred for 5 h at 60° C., filtrated and the solvent was removed in vacuo. The obtained residue of crude 5-(2-cyano-benzyloxy)-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid methyl ester (235 mg, 79%) was dissolved in a mixture of THF, MOH and water (3 ml each), lithium hydroxide (64.1 mg, 2.7 mmol) was added, and the mixture was stirred overnight at room temperature. After evaporation of the solvent the residue was subjected to column chromatography (silica gel, DCM/MOH 9:1) to give 195 mg (86%) of the title compound.

Workup

filtrationfiltrated
customthe solvent was removed in vacuo
additionwas added
stirringthe mixture was stirred overnight at room temperature
customAfter evaporation of the solvent the residue

Sources & evidence

ORD record: ord-0cd5b384b5864f668dd840a368fa0883
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664257B2

Reaction notes

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