3,3-Dimethyl-1-butyne → 3-(3,3-dimethyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1607013ノート

反応式

HRID 1607013 の反応式
Br[C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[N:8]([CH3:17])[CH2:7][C:6]=12.[CH3:18][C:19]([CH3:23])([CH3:22])[C:20]#[CH:21]>C(NCC)C.C(Cl)CCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:18][C:19]([CH3:23])([CH3:22])[C:20]#[C:21][C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[N:8]([CH3:17])[CH2:7][C:6]=12

参加物

7

反応物 2

HCID 135123,3-Dimethyl-1-butyneHCID 198515313-bromo-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

生成物 1

HCID 198515703-(3,3-dimethyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 111,2-Dichloroethane溶媒HCID 8021Diethylamine溶媒

実験手順

2.92 g (10 mmol) of 3-bromo-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to 80° in a pressure tube for 24 hours with 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride, 30 mg of copper(I) iodide and 2.5 ml (20 mmol) of 3,3-dimethyl-1-butyne in 30 ml of diethylamine and 10 ml of ethylene chloride. The reaction mixture was evaporated, the residue was taken up in methylene chloride and washed with water. The organic solution was dried over magnesium sulphate and filtered through a silica gel pad. By crystallization from hexane there was obtained 3-(3,3-dimethyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 148°-150°.

後処理

  1. customThe reaction mixture was evaporated
  2. washwashed with water
  3. dry with materialThe organic solution was dried over magnesium sulphate
  4. filtrationfiltered through a silica gel pad
  5. customBy crystallization from hexane

出典と根拠

ORDレコード
ord-677a825695464d80acee52743c509873
出典データセット
uspto-grants-1989_09
特許番号
US04863920

反応ノート

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