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

HRID 2382090ノート

反応式

HRID 2382090 の反応式
[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

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 44549958HCID 44549958、化合物

生成物 1

HCID 685567693-Methyl-5-trifluoromethyl-indol-1-ylamine収率 52%

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8298464c34864bee9fb8c42bad62ee8f
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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