Bromomethylcyclopropane → 8-chloro-6-(cyclopropylmethyl)benzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398320Notes

Reaction equation

HRID 1398320 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1.[CH:17]1([CH2:20]Br)[CH2:19][CH2:18]1>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[N:7]([CH2:20][CH:17]3[CH2:19][CH2:18]3)[C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 867103228-chlorobenzo[c][2,7]naphthyridin-5(6H)-one

Product 1

HCID 867103258-chloro-6-(cyclopropylmethyl)benzo[c][2,7]naphthyridin-5(6H)-oneYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-chlorobenzo[c][2,7]naphthyridin-5(6H)-one (100 mg, 0.434 mmol) (as prepared in Ex. 12, Part B) in anhydrous DMF (2 mL) at 0° C. was added cyclopropyl methyl bromide (0.088 g, 0.650 mmol) under nitrogen. The reaction mixture was allowed to warm to RT and stirred for 12 h. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to 8-chloro-6-(cyclopropylmethyl)benzo[c][2,7]naphthyridin-5(6H)-one (100 mg, 0.351 mmol, 81% yield, 53% pure by LC/MS). LC/MS (ESI) m/e 285.1 [(M+H)+, calcd for C16H14ClN2O 285.1]; LC/MS retention time (method D): tR=0.91 min.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate

Sources & evidence

ORD record
ord-adf9a7f84b74459fb3a4553a336f3bc6
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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