Sodium hydride → HCID 68094318, compound

HRID 1843997Notes

Reaction equation

HRID 1843997 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]=[CH:12][NH:13][C:14](=[O:15])[C:5]=3[C:4]=2[CH:3]=1.Cl[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:6]3[CH:11]=[CH:12][NH:13][C:14](=[O:15])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 59198430HCID 59198430, compound

Product 1

HCID 68094318HCID 68094318, compoundYield 65.21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Fluoro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-64a: 0.15 g, 0.00074 mol) was reacted with 1-(chloromethyl)-4-methoxybenzene (0.14 g, 0.00092 mol), NaH (0.058 g, 0.058 mol) and DMF (10 mL) to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in DCM) afforded 0.15 g of the product (65.21% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% methanol in DCM)

Sources & evidence

ORD record
ord-5484ef55c07645bca02de40d23770035
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…