Water → 6-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(4-methyloxazol-5-yl)methyl]-1H-pyrido[4,3-b]indol-1-one

HRID 2081214ノート

反応式

HRID 2081214 の反応式
[H-].[Na+].[F:3][C:4]1[C:12]2[N:11]([CH3:13])[C:10]3[CH2:14][CH2:15][NH:16][C:17](=[O:18])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl[CH2:20][C:21]1[O:25][CH:24]=[N:23][C:22]=1[CH3:26].O>COCCOC>[F:3][C:4]1[C:12]2[N:11]([CH3:13])[C:10]3[CH2:14][CH2:15][N:16]([CH2:20][C:21]4[O:25][CH:24]=[N:23][C:22]=4[CH3:26])[C:17](=[O:18])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydride2 回HCID 2054855-(Chloromethyl)-4-methyl-1,3-oxazoleHCID 157125046-Fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one

生成物 1

HCID 157125256-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(4-methyloxazol-5-yl)methyl]-1H-pyrido[4,3-b]indol-1-one収率 76.6%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Sodium hydride (73% dispersion in oil; 167 mg) was added to a stirred suspension of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (500 mg) in dry DME (150 ml), and the suspension was stirred at 60° under nitrogen for 6 h. 5-Chloromethyl-4-methyloxazole (440 mg) was then added and the mixture was stirred overnight at 60°. A further quantity of sodium hydride (73% dispersion in oil; 84 mg) was added and the mixture was stirred for 3 h, and then cooled (0°). Water (200 ml) was added, and the mixture was extracted with dichloromethane (3×200 ml). The combined organic extracts were concentrated in vacuo and the residue was purified by FCC eluting with System A (100:8:1) to give the title compound (550 mg) as a solid, m.p. 158°-161°.

後処理

  1. stirringthe mixture was stirred overnight at 60°
  2. stirringthe mixture was stirred for 3 h
  3. temperaturecooled (0°)
  4. extractionthe mixture was extracted with dichloromethane (3×200 ml)
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customthe residue was purified by FCC
  7. washeluting with System A (100:8:1)

出典と根拠

ORDレコード
ord-93ffe51ec0074f0cad1bf2034c275454
出典データセット
uspto-grants-1993_02
特許番号
US05183820

反応ノート

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