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

HRID 501184

反応式

HRID 501184 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ce5ff47340fc4caebd90296dc89a67f2
出典データセット
uspto-grants-2010_08
特許番号
US07772245B2

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