Potassium Carbonate → N-(4-ethynyl-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamide

HRID 1255147Notes

Reaction equation

HRID 1255147 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([CH:12]=O)[N:11]=1)=[O:5].[N+](=[C:31](P(=O)(OC)OC)C(=O)C)=[N-].C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[C:12]([C:10]1[N:11]=[C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:27][CH:26]=[CH:25][C:24]=2[F:28])[S:8][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)#[CH:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24765490HCID 24765490, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 24765970N-(4-ethynyl-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamideYield 20.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Into a solution of Compound 67 (50.0 mg, 0.12 mmol) and dimethyl 1-diazo-2-oxopropylphosphonate (46.0 mg, 0.24 mmol) in MeOH (1.00 mL) was added K2CO3 (50.0 mg, 0.36 mmol) was added. The mixture was stirred at room temperature overnight, diluted with CH2Cl2, washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified on silica to give Compound 104 (10.0 mg).

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica

Sources & evidence

ORD record
ord-eda6d6380be64354bc0358997f811cbf
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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