Nitrogen → HCID 86700717, 화합물

HRID 572480

반응식

HRID 572480 반응식
Br[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[O:4][C:3]=1[C@H:13]([OH:33])[CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[CH3:41].N#N.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Si:16]([O:15][CH2:14][C@H:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:7]([C:2]=1[C:37]1[CH:38]=[CH:39][C:40]([CH3:41])=[C:35]([CH3:34])[CH:36]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)[OH:33])([C:29]([CH3:30])([CH3:31])[CH3:32])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343483,4-Dimethylphenylboronic acidHCID 68294919HCID 68294919, 화합물

생성물 1

HCID 86700717HCID 86700717, 화합물수율 62%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-bromo-3-((1R)-2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-1-hydroxyethyl)-1H-2-benzopyran-1-one (142 mg, 0.271 mmol) and 3,4-dimethylphenylboronic acid (61.0 mg, 0.407 mmol) in N,N-Dimethylformamide (DMF) (2.5 mL) was degassed with N2 for 10 min. The reaction mixture was treated with 2M Na2CO3 (149 μl, 0.298 mmol) and Pd(PPh3)4 (16 mg, 0.014 mmol) and irradiated in the microwave for 20 min at 120° C. The reaction mixture was diluted with EtOAc, and washed with saturated aqueous NH4Cl, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-30%) to afford the title compound (92 mg, 0.168 mmol, 62% yield) as a white solid: Rt=1.31, 1.33 (atropisomers), ES+ MS: 571 (M+23).

후처리

  1. customirradiated in the microwave for 20 min at 120° C
  2. washwashed with saturated aqueous NH4Cl, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-30%)

출처 및 근거

ORD 기록
ord-73385b61a6f841aebf7c2ec077c97425
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029391B2

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