Sodium hydride → 6-(2,5-dichlorobenzyl)-1-methyl-1,6-dihydro-3H-furo[3',4':5,6]pyrido[3,4-b]indol-3-one

HRID 992563Notes

Reaction equation

HRID 992563 reaction equation
[CH3:1][CH:2]1[C:6]2[C:7]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][C:8]=3[CH:16]=[N:17][C:5]=2[C:4](=[O:18])[O:3]1.[H-].[Na+].[Cl:21][C:22]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:23]=1[CH2:24]Cl>CN(C=O)C>[Cl:21][C:22]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:23]=1[CH2:24][N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:7]2[C:6]3[CH:2]([CH3:1])[O:3][C:4](=[O:18])[C:5]=3[N:17]=[CH:16][C:8]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 759762,5-Dichlorobenzyl chlorideHCID 10014421HCID 10014421, compound

Product 1

HCID 184122256-(2,5-dichlorobenzyl)-1-methyl-1,6-dihydro-3H-furo[3',4':5,6]pyrido[3,4-b]indol-3-oneYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(2,5-Dichlorobenzyl)-1-methyl-1,6-dihydro-3H-furo[3′,4′:5,6]pyrido[3,4-b]indol-3-one was prepared using Method A from 1-methyl-1,6-dihydro-3H-furo[3′,4′:5,6]pyrido[3,4-b]indol-3-one (9 mg, 0.038 mmol), NaH (0.046 mmol, 2 mg of 60 wt. % suspension in mineral oil) and 2,5-dichlorobenzyl chloride (9 mg, 0.046 mmol) in DMF (1 mL). Purification of the crude product by preparative thin layer chromatography with hexane/ether (2:1) as eluent furnished the desired product (5 mg, 33% yield) as a yellow solid. 1H NMR (CDCl3) δ8.93 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H), 7.37-7.46 (m, 3H), 7.16 (d,J=2.2 Hz, 1H), 6.42 (d,J=2.2 Hz, 1H), 6.05 (q,J=6.6 Hz, 1H), 5.70 (s, 2H), 1.92 (d,J=6.6 Hz, 3H); MS (APCI; (M+H)+) m/z 397.

Workup

  1. custom6-(2,5-Dichlorobenzyl)-1-methyl-1,6-dihydro-3H-furo[3′,4′:5,6]pyrido[3,4-b]indol-3-one was prepared
  2. customPurification of the crude product by preparative thin layer chromatography with hexane/ether (2:1) as eluent

Sources & evidence

ORD record
ord-551ea6cad52041f1ad7e2c9f9e7ca982
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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