Trifluoroacetic acid → HCID 59375136、化合物

HRID 661835ノート

反応式

HRID 661835 の反応式
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH:17](O)[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66606820HCID 66606820、化合物

生成物 1

HCID 59375136HCID 59375136、化合物収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Step 3 A solution of crude 2-(3-bromo-2-methylphenyl)-3-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (600 mg, 1.806 mmol) in DCM (30 mL) was treated with triethylsilane (15 mL, 94 mmol) and the resulting mixture was treated slowly with TFA (1.392 mL, 18.06 mmol). The mixture was stirred at rt for 2 h, then was concentrated and the residue was dissolved in DCM. The solution was washed with NaHCO3 (aq) and water, then was dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 to 60:40 hexane-EtOAc) to give 2-(3-bromo-2-methylphenyl)isoquinolin-1(2H)-one as a white solid (380 mg, 67%). Mass spectrum m/z 314, 316 (M+H)+.

後処理

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in DCM
  3. washThe solution was washed with NaHCO3 (aq) and water
  4. customwas dried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (
  7. washeluting with a gradient from 80:20 to 60:40 hexane-EtOAc)

出典と根拠

ORDレコード
ord-5a734ef6e4cb4be7881929fc1d306468
出典データセット
uspto-grants-2011_12
特許番号
US08084620B2

反応ノート

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