Sodium hydride → HCID 86663043, compound

HRID 2410793Notes

Reaction equation

HRID 2410793 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:18]([O:20][CH3:21])=[O:19])[C:7]2[NH:8][C:9]3[CH:10]=[C:11]([Cl:17])[CH:12]=[CH:13][C:14]=3[C:15]=2[N:16]=1.Cl[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([C:18]([O:20][CH3:21])=[O:19])[C:7]2[N:8]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:9]3[CH:10]=[C:11]([Cl:17])[CH:12]=[CH:13][C:14]=3[C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 86663042HCID 86663042, compound

Product 1

HCID 86663043HCID 86663043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.62 g, 15 mmol, 60% oil dispersion) was added to a stirred solution of methyl 2-bromo-7-chloro-5H-pyrido[3,2-b]indole-4-carboxylate (3.5 g, 10.3 mmol) in dry DMF (30 mL) under nitrogen in an ice bath. After 5 min, 1-(chloromethyl)-4-methoxybenzene (1.82 mL, 13 4 mmol) was added and the reaction was removed from the bath and left stirring at RT overnight. The reaction was diluted with EtOAc, washed with water (4×) and then brine. Removal of the solvent followed by step gradient silica gel radial chromatography with hexane containing 25 to 50% DCM afforded impure methyl 2-bromo-7-chloro-5-(4-methoxybenzyl)-5H-pyrido[3,2-b]indole-4-carboxylate (4.0 g) as a light yellow fully solid that was used as such. MS (ESI) m/z 460.95 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.31 (1H, d, J=8.24 Hz), 7.69 (1H, s), 7.47 (1H, d, J=1.53 Hz), 7.34 (1H, dd, J=8.39, 1.68 Hz), 6.78-6.82 (2H, m), 6.73-6.76 (2H, m), 5.63 (2H, s), 3.78 (3H, s), 3.73 (3H, s).

Workup

  1. customthe reaction was removed from the bath
  2. waitleft
  3. additionThe reaction was diluted with EtOAc
  4. washwashed with water (4×)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-3a4179b4ecad4a08beae1e4c4b089deb
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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