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Triphenylphosphine → 6,7-Dimethoxy-1-[1,1';4',1'']terphenyl-4-ylmethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 2238353
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HRID 2238353 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:20][CH3:21])=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:20][CH3:21])=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:42]2[CH:43]=[CH:44][C:39]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:40][CH:41]=2)=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 516892Sodium BicarbonateHCID 589064711-(4-Bromo-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

생성물 1

HCID 589064756,7-Dimethoxy-1-[1,1';4',1'']terphenyl-4-ylmethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 3776Isopropanol용매

실험 절차

6,7-Dimethoxy-1-[1,1′;4′,1″]terphenyl-4-ylmethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (12) was prepared as follows: A mixture of 0.462 g (1 mmol) of 1-(4-Bromo-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester and 0.297 g (1.5 mol. equiv.) of 4-biphenylboronic acid in 4 ml of isopropanol was stirred under argon at room temperature for 30 min. To this mixture, 1 mg (0.45 mol %) of Palladium(II)acetate, 4 mg (1.3 mol %) of triphenylphosphine, and 0.6 ml (1.2 mol. equiv.) of 2M sodium bicarbonate aqueous solution were added successively and the mixture was refluxed with stirring for 6 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between 50 ml of ethyl acetate and 25 ml of 5% sodium hydroxide aqueous solution. After shaking, the organic layer was washed with water (25 ml) and brine (25 ml), and then dried with sodium sulfate. The solvent was evaporated under reduced pressure and the remaining oil was crystallized by trituration with n-hexanes. The solid was recrystallized using ethyl acetate\n-hexanes mixture to give 0.40 g (75%) of white solid, mp 153-155° C.

후처리

  1. temperaturethe mixture was refluxed
  2. stirringwith stirring for 6 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between 50 ml of ethyl acetate and 25 ml of 5% sodium hydroxide aqueous solution
  5. stirringAfter shaking
  6. washthe organic layer was washed with water (25 ml) and brine (25 ml)
  7. dry with materialdried with sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe remaining oil was crystallized by trituration with n-hexanes
  10. customThe solid was recrystallized

출처 및 근거

ORD 기록
ord-a8b32db3bcac462c9f7ed11111e3dbe6
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07718672B2

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