N-[4-(2-Benzyloxy-4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide → N-[4-(4-Fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878026노트

반응식

HRID 878026 반응식
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:22]([CH3:39])[C:23](=[O:38])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:15][C:13]1[CH:12]=[CH:11][C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N:22]([CH3:39])[C:23](=[O:38])[C:24]2[CH:25]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=2)=[C:9]([OH:8])[CH:14]=1

참가 물질

5

반응물 2

HCID 60197400N-[4-(2-Benzyloxy-4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 136209610N-[4-(4-Fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide수율 83.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of N-[4-(2-benzyloxy-4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide (65 mg, 0.118 mmol, example 43) in MeOH (10 mL) was purged with argon for 20 minutes before 10% Pd—C (10 mg) was added. The resulting reaction mixture was hydrogenated under balloon pressure hydrogen at 25° C. for 16 hours. The reaction mixture was filtered through a bed of celite and the residue was further washed with EtOAc. The combined filtrate was concentrated in vacuo, and the crude material thus obtained was purified by column chromatography over silica gel (25-35% EtOAc in n-hexane) to give 45 mg of the desired compound. Off-white solid (60%). MS (ESI): m/z=459.0 [M+H]+.

후처리

  1. additionwas added
  2. customThe resulting reaction mixture
  3. filtrationThe reaction mixture was filtered through a bed of celite
  4. washthe residue was further washed with EtOAc
  5. concentrationThe combined filtrate was concentrated in vacuo
  6. customthe crude material thus obtained
  7. customwas purified by column chromatography over silica gel (25-35% EtOAc in n-hexane)

출처 및 근거

ORD 기록
ord-2a64410e55e64f6f843a4bf806b56d23
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987307B2

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