Dimethylformamide → 1-(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol

HRID 1400508ノート

反応式

HRID 1400508 の反応式
[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[H-].[Na+].[O:17]1[CH2:19][CH:18]1[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.[CH3:26]N(C=O)C>>[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[N:6]([CH2:19][C:18]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)([OH:17])[CH3:26])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 974242-methyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indoleHCID 109534834-(Oxiran-2-yl)pyridine

生成物 1

HCID 497795901-(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol

実験手順

2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (740 mg, 3.9 mmol) was dissolved in DMF and the mixture stirred for 5 min. NaH (60% in oil) (468 mg, 11.7 mmol) was added and the mixture stirred for 10 min., followed by 4-(oxiran-2-yl)pyridine (1.0 g, 7.9 mmol) and the mixture stirred at RT for 3 h. The progress of reaction was monitored by TLC. The reaction mixture was poured into ice water and filtered. The filtrate was washed with water and concentrated. The residue was recrystallized from ether to get pure product. 1H NMR (CD3OD, HCl salt) δ (ppm): 8.70 (d, 2H), 8.20 (d, 2H), 7.40 (m, 1H), 7.10 (m, 1H), 7.0 (m, 2H), 4.70 (d, 1H), 4.45 (m, 2H), 4.38 (m, 1H), 3.90 (m, 1H), 3.45 (m, 2H), 3.40 (m, 1H), 3.10 (s, 3H), 1.70 (d, 3H).

後処理

  1. stirringthe mixture stirred for 10 min.
  2. stirringthe mixture stirred at RT for 3 h
  3. customThe progress of reaction
  4. filtrationfiltered
  5. washThe filtrate was washed with water
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ether
  8. customto get pure product

出典と根拠

ORDレコード
ord-4215b5a200f74d0fbef1fbc2cb93af36
出典データセット
uspto-grants-2014_12
特許番号
US08906925B2

反応ノート

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