Methanol → Methyl Isoquinoline-4-carboxylate

HRID 1470481ノート

反応式

HRID 1470481 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[CH:3][N:2]=1.[CH3:14]CN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([O:13][CH3:14])=[O:12])=[CH:3][N:2]=1

参加物

7

反応物 4

HCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 459768Isoquinoline-4-carboxylic acid

生成物 1

HCID 11830161Methyl Isoquinoline-4-carboxylate収率 54.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of isoquinolin-4-carboxylic acid (Intermediate-14) (1.2 g, 6.9 mmol) in CH2Cl2 (10 mL) was added, EDCI (1.3 g, 8.3 mmol), HOBt (1.12 g, 8.3 mmol), DMAP (84 mg, 0.7 mmol) and the mixture was stirred at RT for 20 min. To this, MeOH (0.33 g, 10.4 mmol) was added and the reaction mixture was further stirred at RT for overnight. It was diluted with CH2Cl2 (100 mL) and washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give crude product that was purified by flash column chromatography (10% EtOAc:Hexanes) to give the desired product (700 mg, 54%) as pale yellow solid.

後処理

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product that
  7. customwas purified by flash column chromatography (10% EtOAc:Hexanes)

出典と根拠

ORDレコード
ord-adbc1a2304b14efdb89cd11e3e8e9b26
出典データセット
uspto-grants-2015_04
特許番号
US09006442B2

反応ノート

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