Lithium Hydroxide → HCID 59408767, compound

HRID 1188122Notes

Reaction equation

HRID 1188122 reaction equation
[Li+].[OH-].Br[C:4]1[N:9]=[C:8]([NH:10][C:11]([C:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:15]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[N:14]=2)=[O:12])[CH:7]=[CH:6][CH:5]=1>C1COCC1.O>[CH2:16]([NH:15][C:4]1[N:9]=[C:8]([NH:10][C:11]([C:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:15]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[N:14]=2)=[O:12])[CH:7]=[CH:6][CH:5]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59408770HCID 59408770, compound

Product 1

HCID 59408767HCID 59408767, compoundYield 123.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

LiOH (120 mg, 5 mmol) was added to a solution of ethyl 5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate 3 (1.1 g 3.4 mmol) in THF/H2O (1:1, 5 ml). The reaction mixture was stirred over night. The clear solution was concentrated, and suspended in chloroform (25 ml), The solid was filtered off and dried under vacuum to give 5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid 4 (987 mg, 99%) as a white solid. Mp. 188-190° C.

Workup

  1. concentrationThe clear solution was concentrated
  2. filtrationThe solid was filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-06836dc590cf45b5aa61200a612568c1
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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