Boron tribromide → 9-Hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

HRID 1400177ノート

反応式

HRID 1400177 の反応式
C[O:2][C:3]1[C:4]2[C:5]3[N:16]=[CH:15][S:14][C:6]=3[NH:7][C:8](=[O:13])[C:9]=2[CH:10]=[CH:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]2[C:5]3[N:16]=[CH:15][S:14][C:6]=3[NH:7][C:8](=[O:13])[C:9]=2[CH:10]=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 580160499-methoxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

生成物 1

HCID 580160609-Hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 9-methoxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one (0.048 g, 0.21 mmol) and CH2Cl2 (2 ml) was added boron tribromide (1.05 ml of 1M sol. in CH2Cl2, 1.05 mmol), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was evaporated, methanol (2 ml) was added, the resulting mixture stirred for 1 hour and then evaporated. The resulting solid was purified by flash chromatography on SiO2 gel to yield the title compound (0.042 g, a 90% yield) as a solid. m.p.>250° C.; 1H NMR (400 MHz, DMSO) δ 7.28 (d, 1H, Ar), 7.47 (t, 1H, Ar), 7.75 (d, 1H, Ar), 9.06 (s, 1H, 2-CH), 10.36 (s, 1H, OH), 12.41 (s, 1H, NH).

後処理

  1. customThe reaction mixture was evaporated
  2. additionmethanol (2 ml) was added
  3. stirringthe resulting mixture stirred for 1 hour
  4. customevaporated
  5. customThe resulting solid was purified by flash chromatography on SiO2 gel

出典と根拠

ORDレコード
ord-0acb305522e042f48f24d512ddd4006d
出典データセット
uspto-grants-2014_12
特許番号
US08906935B2

反応ノート

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