Sodium hydride → methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

HRID 992560

반응식

HRID 992560 반응식
[H-].[Na+].[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]([C:16]([O:18][CH3:19])=[O:17])[N:4]=1.[Na].C1C2NC3C(=CC=CC=3)C=2C=CN=1.[Cl:34][C:35]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:36]=1[CH2:37]Cl>CN(C=O)C.O>[Cl:34][C:35]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:36]=1[CH2:37][N:14]1[C:15]2[CH:3]=[N:4][C:5]([C:16]([O:18][CH3:19])=[O:17])=[CH:6][C:7]=2[C:8]2[C:13]1=[CH:12][CH:11]=[CH:10][CH:9]=2

참가 물질

8

반응물 5

HCID 24758Sodium hydrideHCID 64961Beta-CarbolineHCID 759762,5-Dichlorobenzyl chlorideHCID 107704Methyl 9H-pyrido(3,4-b)indole-3-carboxylateHCID 5360545Sodium

생성물 1

HCID 9908122methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of sodium hydride (1.60 g of 60% dispersion in oil, 0.04 mol) in dry DMF (60 mL) was added methyl 9H-β-carboline-3-carboxylate (8.7 g, 0.0385 mol) at −20° C. with stirring. The mixture was allowed to warm to room temperature with stirring under nitrogen. After stirring for 10 minutes at room temperature, formation of the sodium salt of the β-carboline appeared to be complete, resulting in a clear brown solution. The reaction mixture was cooled in an ice bath, 2,5-dichlorobenzyl chloride (7.82 g, 0.040 mol) was added, and the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with water (200 mL), filtered, and the cake washed with water, ethyl acetate, ether, and dried, affording 13.05 g (88%) of the title product. 1H NMR (CDCl3) δ8.88 (s, 1H), 8.78 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.45-7.35 (m, 3H) 7.18 (dd, J=8.2, 1.7 Hz,1H), 6.52 (s, 1H), 5.56 (s, 2H), 4.06 (s, 3H); MS (APCI; (M+H)+) m/z 385.

후처리

  1. stirringwith stirring under nitrogen
  2. stirringAfter stirring for 10 minutes at room temperature
  3. customresulting in a clear brown solution
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. temperatureto warm to room temperature
  6. stirringstirred overnight
  7. filtrationfiltered
  8. washthe cake washed with water, ethyl acetate, ether
  9. customdried

출처 및 근거

ORD 기록
ord-d9f8c7acaab742b78147fe775900c25b
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469021B1

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