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

HRID 891019Notes

Reaction equation

HRID 891019 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-d79a00a32a034d4b86df8ab874d147f0
Source dataset
uspto-grants-2006_02
Patent number
US07001912B2

Reaction notes

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