Water → Ethyl 9-(3-chloro-2,6-difluorobenzyl)-9H-beta-carboline-3-carboxylate

HRID 722124노트

반응식

HRID 722124 반응식
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:2]=1.[H-].[Na+].[Cl:21][C:22]1[C:23]([F:31])=[C:24]([C:27]([F:30])=[CH:28][CH:29]=1)[CH2:25]Br.O>CN(C=O)C>[Cl:21][C:22]1[C:23]([F:31])=[C:24]([C:27]([F:30])=[CH:28][CH:29]=1)[CH2:25][N:12]1[C:13]2[CH:1]=[N:2][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 27735502-(Bromomethyl)-4-chloro-1,3-difluorobenzene

생성물 1

HCID 21883401Ethyl 9-(3-chloro-2,6-difluorobenzyl)-9H-beta-carboline-3-carboxylate수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (440 mg, 1.83 mmol) in DMF (5 mL) under a nitrogen atmosphere was added NaH (73.3 mg, 60% in mineral oil, 1.83 mmol) portionwise, followed by 3-chloro-2,6-difluorobenzyl bromide (442 mg, 1.83 mmol). Stirring was continued for 22 hours at ambient temperature, water (30 mL) was then added to the mixture. The precipitate was filtered, washed with water and dried to give the title product (0.55 g, 68%). 1H NMR (400 MHz, CD3OD): δ 9.04 (1H, s), 8.86 (1H, s), 8.26 (1H, d, J=8 Hz), 6.98–7.69 (5H, m), 5.82 (2H, s), 4.44 (2H, q, J=8 Hz), 1.43 (3H, t, J=8 Hz).

후처리

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

출처 및 근거

ORD 기록
ord-22b87cf42064460d82aef7ed2499ce86
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138408B2

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