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N-methyl-2-pyrrolidone → 6-[10-Chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-5-methylpyridine-3-carbonitrile

HRID 1399227
ノート
印刷プレビュー

反応式

HRID 1399227 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:28])[C:5]([N:8]2[C:14]3=[N:15][C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:17]=4[N:13]3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:29][N:30]1CCCC1=O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[Cl:22][C:21]1[C:16]2[N:15]=[C:14]3[N:8]([C:5]4[N:6]=[CH:7][C:2]([C:29]#[N:30])=[CH:3][C:4]=4[CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[C:17]=2[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:19][CH:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 13387N-methyl-2-pyrrolidoneHCID 577864001-(5-bromo-3-methylpyridin-2-yl)-10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

生成物 1

HCID 577859886-[10-Chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-5-methylpyridine-3-carbonitrile収率 48%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 178418397
HCID 178418397、化合物
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-(5-bromo-3-methylpyridin-2-yl)-10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (463 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium (116 mg, 0.10 mmol) and zinc cyanide (176 mg, 1.5 mmol) in 1-methyl-2-pyrrolidinone (2.0 mL) was stirred at 100° C. for 14 hr. The mixture was diluted with ethyl acetate, filtered through a pad of celite, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture followed by recrystallization from ethyl acetate/isopropyl ether to afford the title compound (195 mg, 48%) as a colorless solid.

後処理

  1. filtrationfiltered through a pad of celite
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture
  6. customfollowed by recrystallization from ethyl acetate/isopropyl ether

出典と根拠

ORDレコード
ord-6701e1e882f34416bd586e80f7ec944c
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901141B2

反応ノート

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