3-chloro-1H-indole-4-carbonitrile → HCID 84022392, 화합물

HRID 475170노트

반응식

HRID 475170 반응식
[Cl:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][CH:3]=1>N.CO.O.[Ni]>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][NH2:12])[NH:4][CH:3]=1

참가 물질

6

반응물 1

HCID 866947173-chloro-1H-indole-4-carbonitrile

생성물 1

HCID 84022392HCID 84022392, 화합물수율 98.2%

시약·촉매·용매 4

HCID 935Nickel촉매HCID 222Ammonia용매HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of 3-chloro-1H-indole-4-carbonitrile (630.0 mg, 3.57 mmol) in ammonia in MeOH (2M, 45 mL) was added Raney Ni (3.05 g) in water (2 mL). The reaction mixture was then hydrogenated under H2 balloon at 1 atm for 20 h. The reaction mixture was filtered through a pad of Celite®, and the pad was washed alternatively with MeOH (10 mL×3) and water (10 mL×3). Volatile solvents were removed from the filtrate. The remaining crude was extracted with EtOAc (3×75 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. Crystallization from ether/heptane afforded (3-chloro-1H-indol-4-yl)methanamine (133) as a white solid (633 mg, 98.2%). 1H NMR (400 MHz, DMSO) δ 11.33 (br s, 1H), 7.44 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.11-7.01 (m, 2H), 4.18 (s, 2H), 1.73 (br s, 2H).

후처리

  1. customfor 20 h
  2. filtrationThe reaction mixture was filtered through a pad of Celite®
  3. washthe pad was washed alternatively with MeOH (10 mL×3) and water (10 mL×3)
  4. customVolatile solvents were removed from the filtrate
  5. extractionThe remaining crude was extracted with EtOAc (3×75 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customCrystallization from ether/heptane

출처 및 근거

ORD 기록
ord-af03cfb4a8b4418bbe8073b75a65e9a7
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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