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 2068594노트

반응식

HRID 2068594 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-bb9add7ce3014d93859927942e6edd2f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299023B2

반응 노트

불러오는 중…