Cesium fluoride → 4-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)benzaldehyde

HRID 501184

반응식

HRID 501184 반응식
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.[F-].[Cs+]>CN(C=O)C.O.CCOC(C)=O>[CH2:1]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 680234-FluorobenzaldehydeHCID 107838Tetrahydro-beta-carboline

생성물 1

HCID 866075434-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)benzaldehyde수율 31%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

To a solution of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (250 mg, 1.460 mmol) in dry DMF (10 mL) were added 4-fluorobenzaldehyde (181 mg, 1.460 mmol) and CsF (266 mg, 1.752 mmol) and the reaction mixture was stirred at 65° C. for 5 hours. After completion, the reaction mixture was diluted with water (25 mL) and EtOAc (25 mL). The organic layer was separated and the aqueous layer was washed twice with EtOAc. The combined organic layers were dried over anhydrous sodium sulphate and concentrated under vacuum to provide the crude compound. It was then purified by column chromatography using silica gel to obtain 4-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)benzaldehyde (125 mg). 1H NMR (CDCl3+DMSO-D6, 200 MHz) ppm: 9.93 (1H, bs), 9.74 (1H, s), 7.99 (1H, s), 7.76 (2H, d, J=8.8 Hz), 7.44 (1H, m), 7.32 (1H, m), 7.13-6.97 (3H, m), 4.61 (2H, s), 3.86 (2H, t, J=5.6 Hz), 2.93 (2H, m); m/e=277 (M+1).

후처리

  1. customThe organic layer was separated
  2. washthe aqueous layer was washed twice with EtOAc
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customto provide the crude compound
  6. customIt was then purified by column chromatography

출처 및 근거

ORD 기록
ord-ce5ff47340fc4caebd90296dc89a67f2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772245B2

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