Diethyl Ether → 2,6-Difluoro-N-(4-(2-hydroxypropan-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

HRID 1255130Notes

Reaction equation

HRID 1255130 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:10](C(OC)=O)[N:11]=1)=[O:5].[CH3:31][Mg+].[Br-].CC[O:36][CH2:37][CH3:38]>>[F:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:10]([C:37]([OH:36])([CH3:38])[CH3:31])[N:11]=1)=[O:5]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 24765114Methyl 2-(2,6-difluorobenzamido)-5-(3-(trifluoromethyl)phenyl)thiazole-4-carboxylateHCID 178418689HCID 178418689, compound

Product 1

HCID 247655782,6-Difluoro-N-(4-(2-hydroxypropan-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamideYield 91%

Procedure

Into a solution of Compound 35 (100 mg, 0.24 mmol) in 5 mL of Et2O was added dropwise MeMgBr (1.0 M solution in THF, 1.2 mL) at 0° C. The mixture was stirred at room temperature for 1 hour and quenched with 10 mL of H2O. The solution was extracted with Et2O. The combined extracts were dried and concentrated. The residue was purified by column chromatography on silica gel (10-70% EtOAc in hexanes) to give Compound 68 (91 mg, 91%) as a white solid.

Workup

  1. customquenched with 10 mL of H2O
  2. extractionThe solution was extracted with Et2O
  3. customThe combined extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (10-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d3e9e1d0f4d5484bac05672d6e74680a
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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