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Potassium Acetate → (2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-6-YL)boronic acid pinacol ester

HRID 1712946
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인쇄 미리보기

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HRID 1712946 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]2.Br[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2.[B:37]1([B:46]2[O:50][C:49]([CH3:52])([CH3:51])[C:48]([CH3:54])([CH3:53])[O:47]2)[O:41][C:40]([CH3:43])([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]1.C([O-])(=O)C.[K+]>CN(C=O)C.CCOC(C)=O>[CH3:44][C:39]1([CH3:45])[C:40]([CH3:43])([CH3:42])[O:41][B:37]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]3)[O:38]1.[CH3:52][C:49]1([CH3:51])[C:48]([CH3:53])([CH3:54])[O:47][B:46]([C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:29]=2[CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)[O:50]1
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참가 물질

8

반응물 4

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 49761184tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 59463272Tert-butyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

생성물 2

HCID 52987621(2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-6-YL)boronic acid pinacol ester
HCID 66734880
tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

A solution of tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (19.5 mmol), bis(pinacolato)diboron (21.4 mmol) and potassium acetate (61 mmol) in DMF (100 mL) was degassed. To this solution was added PdCl2dppf (1:1 complex with DCM, 0.8 mmol). The reaction mixture was heated at 85° C. for 4 hr and then allowed to cool to room temperature and diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. LCMS: (FA) ES+ 360 (for each).

후처리

  1. temperatureto cool to room temperature
  2. washThe solution was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-a55c4fd544d148ee9c20db86cc77cc94
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795249B2

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