Dimethylformamide → 3-Methyl-5-trifluoromethyl-indol-1-ylamine

HRID 2382090노트

반응식

HRID 2382090 반응식
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=2)[NH:6][CH:5]=1.C[N:18](C=O)C>>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:14])[F:15])[CH:11]=2)[N:6]([NH2:18])[CH:5]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 44549958HCID 44549958, 화합물

생성물 1

HCID 685567693-Methyl-5-trifluoromethyl-indol-1-ylamine수율 52%

반응 조건

온도
0 °C

실험 절차

60% NaH (1.21 g, 30.2 mmol) is added to a stirred solution of 3-methyl-5-trifluoromethyl-1H-indole (400 mg, 2.01 mmol) in DMF (6 mL) at 0° C. in portions. The mixture is stirred at 0° C. for 1 h. HOSA (1.14 g, 10.0 mmol) is added in portions at 0° C. and the mixture is allowed to warm to rt over 2 h. The reaction is quenched with aqueous saturated ammonium chloride, extracted with extracted three times with DCM. The combined organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford 3-methyl-5-trifluoromethyl-indol-1-ylamine (223 mg, 52%). MS: 215 (M+H); 1H NMR (300 MHz, CDCl3): δ=7.84 (s, 1H), 7.48 (s, 2H), 7.04 (s, 1H), 4.77 (s, 2H), 2.34 (s, 3H).

후처리

  1. additionHOSA (1.14 g, 10.0 mmol) is added in portions at 0° C.
  2. temperatureto warm to rt over 2 h
  3. customThe reaction is quenched with aqueous saturated ammonium chloride
  4. extractionextracted
  5. extractionwith extracted three times with DCM
  6. dry with materialThe combined organic layer is dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

출처 및 근거

ORD 기록
ord-8298464c34864bee9fb8c42bad62ee8f
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

반응 노트

불러오는 중…