Methanol → 1-{[ethyl(methyl)amino]acetyl}-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine

HRID 1014314ノート

反応式

HRID 1014314 の反応式
Br[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH3:25][NH:26][CH2:27][CH3:28].CO>ClCCl.CC(=O)OCC.[Pd].C1COCC1>[CH2:27]([N:26]([CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([NH2:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4])[CH3:25])[CH3:28]

参加物

9

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 12219N-MethylethylamineHCID 594418341-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

生成物 1

HCID 594420161-{[ethyl(methyl)amino]acetyl}-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The 1-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (4.0 g, 12.7 mmol) was dissolved in 50 mL of dichloromethane, then K2CO3 (4.4 g, 31.7 mmol) and N-methylethanamine(1.5 g, 25.4 mmol) in 10 mL dichloromethane were added and the reaction was stirred at RT for 3 hours. After filtration, the organic layers were washed with water (2×100 mL) and dried over Na2SO4. The solvent was was removed under reduced pressure and the derived residue (3.4 g, 11.59 mmol) was dissolved in 10 mL of EA, 25 mL of MeOH and 15 mL of THF, then 0.8 g 10% Pd/C was added, the reaction was stirred at RT overnight under H2 pressure (65 psi). The catalyst was removed via filteration, and the solvent was evaporated under reduced pressure to afford 1-{[ethyl(methyl)amino]acetyl}-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine as a yellow solid, 3.0 g (97%).1HNMR (400 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.14 Hz, 3H), 2.20 (s, 3H), 2.46(m, 2H), 2.94 (t, 2 H), 3.16(s, 2H), 3.68 (s, 3H), 4.06 (t, J=8.42 Hz, 2 H), 4.60 (s, 2H), 6.67 (s, 1 H), 7.52 (s, 1 H).

後処理

  1. filtrationAfter filtration
  2. washthe organic layers were washed with water (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was was removed under reduced pressure
  5. stirringthe reaction was stirred at RT overnight under H2 pressure (65 psi)
  6. customThe catalyst was removed via filteration
  7. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-3a358f2a1b3f49efad154a9ef3abcf17
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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