Benzyl Bromide → Methyl 4-(benzyloxy)-7-bromoisoquinoline-3-carboxylate

HRID 1481143노트

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HRID 1481143 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([Br:16])[CH:9]=2)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH:23]1[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=1>CN(C=O)C.CCOC(C)=O.O>[CH2:29]([O:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([Br:16])=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4])[C:26]1[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=1

참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 89813103Methyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

생성물 1

HCID 89812966Methyl 4-(benzyloxy)-7-bromoisoquinoline-3-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of 7-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (955.0 mg, 3.4 mmol), K2CO3 (1.2 g, 8.5 mmol), KI (56.2 mg, 0.3 mmol) and BnBr (0.6 mL, 4.7 mmol) in DMF (17 mL) was stirred at 60° C. for 16 hours. After cooling to room temperature, the mixture was diluted with EtOAc (100 mL) and H2O (100 mL). The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-20% EtOAc/CH2Cl2) to give the title compound in 1.1 g. MS: (+) m/z 372.20 (M+1).

후처리

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-20% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-ee7ddeedfb2a4921a551f0fdb41a90dc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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