2-Fluoro-6-methoxybenzaldehyde → (R)-5-(5-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1-methyl-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole

HRID 1465707노트

반응식

HRID 1465707 반응식
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=O.[CH3:12][N:13]1[C:17]([C@@H:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[N:16][C:15]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[NH:29][N:28]=[C:27]3[C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)=[N:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(Cl)Cl.O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH2:4][N:20]1[CH2:21][CH2:22][CH2:23][C@@H:18]([C:17]2[N:13]([CH3:12])[N:14]=[C:15]([C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[NH:29][N:28]=[C:27]4[C:33]3[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=3)[N:16]=2)[CH2:19]1

참가 물질

7

반응물 3

HCID 27373572-Fluoro-6-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86695582(R)-5-(1-methyl-5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole

생성물 1

HCID 56971413(R)-5-(5-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1-methyl-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole수율 63.6%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Added 2-Fluoro-6-methoxy benzaldehyde (20 mg, 0.129 mmol) to a solution of (R)-5-(1-methyl-5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole (15 mg, 0.0379 mmol) and sodium triacetoxyborohydride (25 mg, 0.118 mmol) in MeOH (4 ml) at room temperature, then stirred for 2 hours. Reaction was diluted with CH2Cl2 (50 ml) and H2O (25 ml), organic layer was separated, dried over Na2SO4, filtered and solvent evaporated. The residue was chromatographed on silica gel eluting with 5% v/v MeOH/CH2Cl2/NH4OH to yield (R)-5-(5-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1-methyl-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole as a white solid (12 mg).

후처리

  1. customReaction
  2. customwas separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customThe residue was chromatographed on silica gel eluting with 5% v/v MeOH/CH2Cl2/NH4OH

출처 및 근거

ORD 기록
ord-b48628639f43466bb4eb1c57bfb8aa56
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999966B2

반응 노트

불러오는 중…