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

HRID 1776159노트

반응식

HRID 1776159 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5367dd6922e94bb4992bd0b2fed31b15
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265769B2

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