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

HRID 1481143ノート

反応式

HRID 1481143 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ee7ddeedfb2a4921a551f0fdb41a90dc
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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