Sodium Carbonate → HCID 178421998, 화합물

HRID 572489노트

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HRID 572489 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Br)=[C:14]([C:20]([CH3:28])([CH3:27])[O:21][SiH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[O:15][C:16]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:38]2[C:39]([CH3:48])=[C:40]3[C:45](=[CH:46][CH:47]=2)[O:44][CH2:43][CH2:42][CH2:41]3)O1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:38]3[C:39]([CH3:48])=[C:40]4[C:45](=[CH:46][CH:47]=3)[O:44][CH2:43][CH2:42][CH2:41]4)=[C:14]([C:20]([CH3:28])([CH3:27])[O:21][SiH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[O:15][C:16]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 574162234,4,5,5-Tetramethyl-2-(5-methylchroman-6-yl)-1,3,2-dioxaborolaneHCID 1317328254-Bromo-3-(2-tert-butylsilyloxypropan-2-yl)-7-phenylmethoxyisochromen-1-one

생성물 1

HCID 178421998HCID 178421998, 화합물수율 14.6%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

To a solution of 7-Benzyloxy-4-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-isochromen-1-one (30 g, 63.1 mmol) and 4,4,5,5-tetramethyl-2-(5-methylchroman-6-yl)-1,3,2-dioxaborolane (51.9 g, 89 mmol) in 1,4-dioxane/H2O (400/100 mL) was added Pd(dppf)Cl2 (4.62 g, 6.31 mmol), Na2CO3 (20 g, 189 mmol), and PPh3 (4.96 g, 18.93 mmol). The resultant mixture was stirred at refluxing under N2. After 12 h, the reaction mixture was cooled to ambient temperature and partitioned between dichloromethane and water. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography column on silica gel to afford title product as a pale solid (5.0 g). LCMS (10-80 AB—2MIN.M): Rt=1.541, purity=93.3%, M+1=542.

후처리

  1. temperatureat refluxing under N2
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography column on silica gel

출처 및 근거

ORD 기록
ord-795f411b8cb642719488469ff3634dfa
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029391B2

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