Sodium hydride → 6-benzyl-8-chlorobenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398312Notes

Reaction equation

[H-].[Na+].[CH2:3]([NH:10][C:11](=[O:26])[C:12]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2F)=[CH:16][CH:15]=[N:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1>[CH2:3]([N:10]1[C:19]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=2[C:17]2[C:12](=[CH:13][N:14]=[CH:15][CH:16]=2)[C:11]1=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of sodium hydride (96 mg, 3.99 mmol) in THF (13 mL) at 0° C. was added a solution of N-benzyl-4-(4-chloro-2-fluorophenyl)nicotinamide (680 mg, 1.995 mmol) in THF (10 mL) dropwise over a period of 10 min. The reaction mixture was stirred at 0° C. for 1 h and then warmed to room temperature and stirred for another 1 h. The reaction mixture was then treated with ice and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (1×5 mL), dried (Na2SO4) and concentrated under reduced pressure to afford crude 6-benzyl-8-chlorobenzo[c][2,7]naphthyridin-5(6H)-one (640 mg, 2.00 mmol, 100%). LC/MS (ESI) m/e 321.0 [(M+H)+, calcd for C19H14ClN2O 321.0]; LC/MS retention time (method A): tR=1.95 min.

Workup

temperaturewarmed to room temperature
stirringstirred for another 1 h
additionThe reaction mixture was then treated with ice
extractionextracted with ethyl acetate (3×5 mL)
washThe combined organic layers were washed with brine (1×5 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-58b474ac21864eb197e96a4f756474f1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

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