Sodium hydride → Ethyl 6-amino-9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

HRID 992564Notes

Reaction equation

HRID 992564 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][C:5]2=1.[H-].[Na+].[Cl:22][C:23]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:24]=1[CH2:25]Cl>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:25][C:24]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:23]=1[Cl:22])[C:10]1[CH:9]=[N:8][C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][C:5]2=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 759762,5-Dichlorobenzyl chlorideHCID 603089Ethyl 6-amino-9H-beta-carboline-3-carboxylate

Product 1

HCID 18412215Ethyl 6-amino-9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 6-amino-9H-β-carboline-3-carboxylate (100 mg, 0.39 mmol), NaH (0.58 mmol, 24 mg of 60 wt. % suspension in mineral oil) and 2,5-dichlorobenzyl chloride (115 mg, 0.59 mmol) in DMF (2 mL), was treated according to Method A. Purification of the crude product by column chromatography on silica with hexane/ethyl acetate (7:3) as eluent furnished the desired product (87 mg, 54% yield) as a yellow solid. 1H NMR (DMSO-d6) δ8.96 (s, 1H), 8.74 (s,1H), 7.60 (d,J=8.6 Hz, 1H), 7.48 (d, 1H), 7.41 (dd, J=8.4 Hz, 2.1Hz, 1H), 7.35 (d, J=8.8 Hz, 1H), 7.01 (d,J=8.6 Hz, 1H), 6.51 (d, J=1.8 Hz, 1H), 5.80 (s, 2H), 5.10 (br s, 1H), 4.37 (q,J=7.0 Hz, 2H), 1.37 (t, J=7.0 Hz, 3H); MS (APCI; (M+H)+) m/z 414.

Workup

  1. additionwas treated
  2. customPurification of the crude product by column chromatography on silica with hexane/ethyl acetate (7:3) as eluent

Sources & evidence

ORD record
ord-237eec4cc52a46abb293319dc3ba68c1
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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