2,2'-Bipyridine → 4-{2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 2112220노트

반응식

HRID 2112220 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[C:33]#[N:34])=[CH:22][CH:23]=3)[CH:18]=[N:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1C1C=CC=CN=1.[BH4-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[CH2:33][NH2:34])=[CH:22][CH:23]=3)[CH:18]=[N:17]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 14742,2'-BipyridineHCID 4311764Sodium borohydrideHCID 674105684-{2-[5-(2-Cyano-4-fluorophenoxy)-indazol-1-yl]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 674116794-{2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester수율 86%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4-{2-[5-(2-cyano-4-fluorophenoxy)-indazol-1-yl]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester (0.160 g, 0.344 mmol), CoBr2 (0.008 g, 0.034 mmol), [2,2′]bipyridinyl (0.016 g, 0.010 mmol) in EtOH (6 mL) was added NaBH4 (0.039 g, 1.0 mmol). The mixture was stirred for 3 hours at room temperature. The reaction was quenched with MeOH (3 mL) and acetic acid (10 drops). The solution was concentrated under reduced pressure and diluted with ethyl acetate. The mixture was washed with aqueous NaHCO3, brine, dried over MgSO4, and concentrated under reduced pressure. The crude oil was chromatographed eluting with 1% triethylamine in ethyl acetate, MeOH/CH2Cl2/hexanes (1:15:15, 1% triethylamine), then MeOH/CH2Cl2/hexanes (1:10:10, 1% triethylamine). The pure product was obtained in 86% yield.

후처리

  1. customThe reaction was quenched with MeOH (3 mL) and acetic acid (10 drops)
  2. concentrationThe solution was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washThe mixture was washed with aqueous NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude oil was chromatographed
  8. washeluting with 1% triethylamine in ethyl acetate, MeOH/CH2Cl2/hexanes (1:15:15, 1% triethylamine)
  9. customThe pure product was obtained in 86% yield

출처 및 근거

ORD 기록
ord-e7b3ec7007f94eb990917fe6a4a05472
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521447B2

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