3-Methoxybenzonitrile → 9-methoxy-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

HRID 926279ノート

反応式

HRID 926279 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][C:8]2=[CH:13]/[C:14](/[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)=[N:15]/[H].C[O:26][C:27]1C=CC=C2[C:28]=1CCN=C2C.[Li+].CC([N-]C(C)C)C.COC1C=C(C=CC=1)C#N>CCOCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]1[C:27](=[O:26])[CH2:28][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH:13]=[C:8]12

参加物

6

反応物 4

HCID 737123-MethoxybenzonitrileHCID 2724682Lithium diisopropylamideHCID 450911955-Methoxy-1-methyl-3,4-dihydroisoquinolineHCID 178506468HCID 178506468、化合物

生成物 1

HCID 733348529-methoxy-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
30 °C

実験手順

(Z)-2-(5-methoxy-3,4-dihydroisoquinolin-1(2H) -ylidene)-1-(3-methoxyphenyl)ethanimine. 1-1. A flask was charged with 5-methoxy-1-methyl-3,4-dihydroisoquinoline (3.0 g, 17.1 mmol) and Et2O (100 mL) under N2 and cooled to 30° C. A 2M solution of LDA (8.56 mL, 17.1 mmol) was added dropwise. The resulting brown suspension was stirred for 30 min at this temperature, and then cooled to −78° C. A solution of 3-methoxybenzonitrile (2.28 g, 17.1 mmol) in Et2O (25 mL) was added dropwise. The mixture was stirred at −78° C. for 1 h, and then allowed to warm to RT and stirred for another 18 h. the mixture was then poured onto H2O and extracted with AcOEt. The org. layers were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (5.9 g) as a brown oil that was used as it is in the next step. UPLC-MS: MS 309.3 (M+H+); UPLC rt 0.73 min.

後処理

  1. temperaturecooled to −78° C
  2. stirringThe mixture was stirred at −78° C. for 1 h
  3. temperatureto warm to RT
  4. stirringstirred for another 18 h. the mixture
  5. additionwas then poured onto H2O
  6. extractionextracted with AcOEt
  7. dry with materiallayers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f3efc88da4c94a439ff63934eaf7836e
出典データセット
uspto-grants-2016_03
特許番号
US09284331B2

反応ノート

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