tert-Butyl piperazine-1-carboxylate → 4-[2-(2-Hydroxy-ethyl)-1-oxo-1,2-dihydro-isoquinolin-7-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 2068594ノート

反応式

HRID 2068594 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]2=[O:12])=[CH:4][CH:3]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:25]([O:24][C:22]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]3=[O:12])=[CH:4][CH:3]=2)[CH2:18][CH2:17]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

参加物

7

反応物 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23665647Potassium tert-butoxideHCID 592382027-Bromo-2-(2-hydroxyethyl)-isoquinolin-1-one

生成物 1

HCID 592381654-[2-(2-Hydroxy-ethyl)-1-oxo-1,2-dihydro-isoquinolin-7-yl]piperazine-1-carboxylic acid tert-butyl ester収率 64.3%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

A solution of compound 6 (6.8 g, 25.4 mmol), tert-butyl piperazine-1-carboxylate (5.68 g, 30.5 mmol), Pd2(dba)3 (775 mg, 0.85 mmol), S-Phos (1.16 g) and t-BuOK (5.7 g, 50.8 mmol) in toluene (100 mL) was heated to 90° C. under nitrogen overnight. Then the mixture was cooled to room temperature and filtered. The filtrate was concentrated, the residue was dissolved in methylene chloride, washed with water, dried (sodium sulfate), concentrated and purified by flash column chromatography (silica gel) to give 7 (6.1 g, 64%)

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel)

出典と根拠

ORDレコード
ord-bb9add7ce3014d93859927942e6edd2f
出典データセット
uspto-grants-2012_10
特許番号
US08299023B2

反応ノート

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