Sodium Bicarbonate → 3-(1-{[8-Fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 411599ノート

反応式

HRID 411599 の反応式
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[NH:24]1[CH2:29][CH:28]=[C:27]([C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[F:23][C:19]1[C:17]2[O:18][CH:13]([CH2:12][N:24]3[CH2:25][CH:26]=[C:27]([C:30]4[C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[NH:32][CH:31]=4)[CH2:28][CH2:29]3)[CH2:14][O:15][C:16]=2[CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 10759436(2R)-8-Fluoro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl 4-methylbenzenesulfonate

生成物 1

HCID 101556703-(1-{[8-Fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

試薬・触媒・溶媒 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

[(2R)-8-Fluoro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl 4-methylbenzenesulfonate (1.2 g, 3.5 mmole) was dissolved in a mixture of dimethylformamide/tetrahydrofuran (1:1 v/v, 30 mL) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.60 g, 3.0 mmole) added, followed by the addition of sodium bicarbonate (0.60 g, 7.1 mmole) and the mixture refluxed under nitrogen for 18 hours. The solvent was evaporated in vacuum, and the residue partitioned between 400 mL each of methylene chloride and water. The organic phase was dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue chromatographed on silica gel using 4% methanol in chloroform as eluant. The product fractions were combined and concentrated in vacuum to give 0.20 g (16%) of the (S)-enantiomer of the title compound as a yellow solid, m.p. 174-177° C.

後処理

  1. additionadded
  2. temperaturethe mixture refluxed under nitrogen for 18 hours
  3. customThe solvent was evaporated in vacuum
  4. customthe residue partitioned between 400 mL each of methylene chloride and water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customthe residue chromatographed on silica gel using 4% methanol in chloroform as eluant
  9. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-0725824d5009453a9a8583fc0820b178
出典データセット
uspto-grants-2003_05
特許番号
US06559169B2

反応ノート

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