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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → Tert-butyl 4-{[6-bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-4-yl]sulfanyl}piperidine-1-carboxylate

HRID 906457
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HRID 906457 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[S:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.Br[CH2:28][C:29]([CH3:40])([CH3:39])[CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:23]([O:22][CH2:20][CH3:28])[CH3:26].[CH3:11][CH2:2][CH2:3][CH:4]([CH3:9])[CH3:5].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:28][C:29]([CH3:40])([CH3:39])[CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34])[CH:6]=[C:5]2[S:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 11780954(3-Bromo-2,2-dimethylpropoxy)(tert-butyl)dimethylsilaneHCID 67130258tert-Butyl 4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfanyl]piperidine-1-carboxylate

생성물 2

HCID 21882825Ether isohexane수율 25%HCID 67390931
Tert-butyl 4-{[6-bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-4-yl]sulfanyl}piperidine-1-carboxylate
수율 96.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of tert-butyl 4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfanyl]piperidine-1-carboxylate (Example 58b, 0.353 g) in DMF (5 mL) was treated with (3-bromo-2,2-dimethylpropoxy)(tert-butyl)dimethylsilane (0.452 g) and cesium carbonate (0.785 g). The mixture was stirred at 80° C. for 16 h, then at 90° C. for 16 h. After cooling to room temperature the reaction mixture was partitioned between water (250 mL) and ethyl acetate (3×250 mL). The combined organics were washed with water (3×200 mL) and brine (3×100 mL), dried (MgSO4), filtered and concentrated. The crude product was dissolved in the minimum amount of DCM and purified (SiO2 chromatography, eluting first with isohexane, then 25% diethyl ether/isohexane) to afford the subtitle compound (0.248 g).

후처리

  1. waitat 90° C. for 16 h
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. customwas partitioned between water (250 mL) and ethyl acetate (3×250 mL)
  4. washThe combined organics were washed with water (3×200 mL) and brine (3×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe crude product was dissolved in the minimum amount of DCM
  9. custompurified (SiO2 chromatography
  10. washeluting first with isohexane

출처 및 근거

ORD 기록
ord-e235ae7e823a40eebc48ef687dc9f235
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012980B2

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