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

HRID 1398320ノート

反応式

HRID 1398320 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-adf9a7f84b74459fb3a4553a336f3bc6
出典データセット
uspto-grants-2014_12
特許番号
US08901305B2

反応ノート

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