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

HRID 501184Notes

Reaction equation

[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

Participants

Conditions

Temperature: 65 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-ce5ff47340fc4caebd90296dc89a67f2
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772245B2

Reaction notes

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