Sodium hydride → HCID 59435985, compound

HRID 1802510Notes

Reaction equation

HRID 1802510 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:28]=[CH:27][C:7]2[N:8]=[C:9]([NH:17][C:18]3[C:23]([Cl:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=3[Cl:26])[C:10]3[CH:11]=[CH:12][NH:13][C:14](=[O:16])[C:15]=3[C:6]=2[CH:5]=1.Cl[CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[Br:3][C:4]1[CH:28]=[CH:27][C:7]2[N:8]=[C:9]([N:17]([C:18]3[C:19]([Cl:26])=[CH:20][C:21]([F:25])=[CH:22][C:23]=3[Cl:24])[CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:10]3[CH:11]=[CH:12][N:13]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:14](=[O:16])[C:15]=3[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 59436052HCID 59436052, compound

Product 1

HCID 59435985HCID 59435985, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of NaH (252 mg, 6.29 mmol) in THF (20 ml) was added 9-bromo-5-[(2,6-dichloro-4-fluorophenyl)amino]benzo[c]-2,6-naphthyridin-1(2H)-one (950 mg, 2.097 mmol) and the mixture was stirred for 5 min. [2-(Chloromethoxy)ethyl](trimethyl)silane (1.116 ml, 6.29 mmol) was added and the mixture was stirred at room temperature overnight. The solution was quenched with MeOH and concentrated under reduced pressure. The residue was purified by flash chromatography (0-30% ethyl acetate in hexanes) to afford the title compound.

Workup

  1. additionwas added
  2. customThe solution was quenched with MeOH
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ef8c6a9076c94e449fd5b8099e00276c
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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