Sodium Bicarbonate → 6-Fluoro-3-[1-(8-methoxy-2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-1H-indole

HRID 411598

反応式

HRID 411598 の反応式
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[F:25][C:26]1[CH:34]=[C:33]2[C:29]([C:30]([C:35]3[CH2:36][CH2:37][NH:38][CH2:39][CH:40]=3)=[CH:31][NH:32]2)=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[F:25][C:26]1[CH:34]=[C:33]2[C:29]([C:30]([C:35]3[CH2:36][CH2:37][N:38]([CH2:12][CH:13]4[O:18][C:17]5[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=5[O:15][CH2:14]4)[CH2:39][CH:40]=3)=[CH:31][NH:32]2)=[CH:28][CH:27]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 11792133[(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate

生成物 1

HCID 102719506-Fluoro-3-[1-(8-methoxy-2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-1H-indole

試薬・触媒・溶媒 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

[(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate (0.30 g, 0.86 mmole), 6-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.60 g, 2.7 mmole) and sodium bicarbonate (0.80 g) were added to a mixture of dimethylformamide/tetrahydrofuran (1:1 v/v, 20 mL) and the reaction mixture was refluxed under nitrogen for 18 hours. The solvent was evaporated and the residue partitioned between 400 mL each of water and methylene chloride. The layers were separated and the methylene chloride solution was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous potassium carbonate and filtered. The filtrate was evaporated in vacuum and the residue crystallized from chloroform containing 3% methanol, giving 0.23 g (68%) of the (S)-enantiomer of the title compound as an off-white solid, m.p. 184-185° C.

後処理

  1. temperaturethe reaction mixture was refluxed under nitrogen for 18 hours
  2. customThe solvent was evaporated
  3. customthe residue partitioned between 400 mL each of water and methylene chloride
  4. customThe layers were separated
  5. washthe methylene chloride solution was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuum
  9. customthe residue crystallized from chloroform containing 3% methanol

出典と根拠

ORDレコード
ord-acc11fd42515437f9500a243b1ae8555
出典データセット
uspto-grants-2003_05
特許番号
US06559169B2

関連ノート

読み込み中…