Potassium Carbonate → HCID 68936624, 화합물

HRID 1260946노트

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HRID 1260946 반응식
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([N:18]([CH3:29])[C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C@H:14]([C:30]3[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=3)[CH2:13]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:37]1(B(O)O)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.CN(C=O)C.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.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([N:18]([CH3:29])[C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C@H:14]([C:30]3[CH:35]=[CH:34][C:33]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:32][CH:31]=3)[CH2:13]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

9

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 68935939HCID 68935939, 화합물

생성물 1

HCID 68936624HCID 68936624, 화합물수율 61%

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 962Water용매2회HCID 1140Toluene용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of the compound obtained in Example 239 (0.20 g), phenylboronic acid (0.066 g), dppf (0.040 g), Pd(OAc)2 (0.008 g) and potassium carbonate (0.050 g) in toluene (3 mL), water (0.3 mL) and DMF (1 mL) was stirred under an argon atmosphere at 100° C. for 10 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, and concentrated. The residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 65→95% ethyl acetate/hexane) to give the title compound (0.12 g, 61%) as a white powder.

후처리

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 65→95% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-12a8e50719744708889c2dc733f2bcb2
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470816B2

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