Potassium Carbonate → 2,6-Difluoro-N-(4-(oxazol-5-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

HRID 1255139Notes

Reaction equation

HRID 1255139 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:13])[N:11]=1)=[O:5].S([CH2:39][N+:40]#[C-:41])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[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:21])([F:22])[F:23])[CH:15]=2)=[C:10]([C:12]2[O:13][CH:41]=[N:40][CH:39]=2)[N:11]=1)=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 24765490HCID 24765490, compound

Product 1

HCID 247655822,6-Difluoro-N-(4-(oxazol-5-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamideYield 72.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Into a solution of Compound 67 (62 mg, 0.15 mmol) in 5 mL of dry methanol was added tosylmethyl isocyanide (35 mg, 0.18 mmol), followed by dry potassium carbonate (25 mg, 0.18 mmol). The reaction mixture was heated to 65° C. for 2 hours. The reaction mixture was dissolved in ethyl acetate, washed each with water and brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (eluted with 10-50% ethyl acetate in hexanes) to give Compound 76 (49 mg, 72%) as a white solid.

Workup

  1. washwashed each with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (eluted with 10-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-eca5028d79de4ffe8c2cacdac2edd003
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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