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Sodium Methoxide → HCID 178517415, compound

HRID 2281917
Notes
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Reaction equation

HRID 2281917 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:18]=[CH:17][O:16][N:15]=3)[N:11]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:10]=2)[N:3]=1.C[O-:28].[Na+]>CO>[F:8][C:7]1[C:2]([OH:28])=[N:3][C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:18]=[CH:17][O:16][N:15]=3)[N:11]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:10]=2)=[N:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 716222913-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2fluorobenzyl)-1H-pyrazol-5-yl)isoxazole2×

Product 1

HCID 178517415HCID 178517415, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2fluorobenzyl)-1H-pyrazol-5-yl)isoxazole (Compound 30, 0.040 g, 0.107 mmol) in 1 mL methanol was added sodium methoxide (0.024 ml, 0.107 mmol) as a 25% weight solution. The reaction was stirred at 40° C. until judged complete by LC/MS. Once complete, the reaction mixture was directly concentrated in vacuo, and the resulting crude oil was purified using silica gel chromatography employing a 0-100% ethyl acetate in hexane gradient to afford the desired compound as a white solid in 55% yield.

Workup

  1. concentrationOnce complete, the reaction mixture was directly concentrated in vacuo
  2. customthe resulting crude oil was purified

Sources & evidence

ORD record
ord-c79fbdf790d64f198e3584f4cfa4c4eb
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139564B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes