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

HRID 1398320노트

반응식

HRID 1398320 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-adf9a7f84b74459fb3a4553a336f3bc6
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901305B2

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