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

HRID 1255130
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HRID 1255130 반응식
[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]
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참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d3e9e1d0f4d5484bac05672d6e74680a
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08455658B2

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