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 878026ノート

反応式

HRID 878026 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-2a64410e55e64f6f843a4bf806b56d23
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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