Sodium Carbonate → HCID 178418705, 화합물

HRID 9337

반응식

HRID 9337 반응식
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C([O-])(=O)C.[K+].C([O:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30](Br)[CH:31]=2)[NH:26]1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl[Pd]Cl>[OH:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:4]3[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[CH:3]=3)[C:8]#[N:9])[CH:31]=2)[NH:26]1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 27833303-Bromo-5-fluorobenzonitrileHCID 178419047HCID 178419047, 화합물

생성물 1

HCID 178418705HCID 178418705, 화합물수율 66%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매2회HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 3-fluoro-5-cyano-bromobenzene (0.4 g, 2.0 mmol) in dry DMF (10 ml) was added diboron pinacolate ester (0.63 g, 2.5 mmol), potassium acetate (0.65 g, 6.7 mmol) and PdCl2 (dppf) (0.2 g) and the reaction was heated to 80° C. under a nitrogen atmosphere. After 8 h. from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (0.2 g, 0.5 mmol), PdCl2 (dppf) (0.05 g) and sodium carbonate (1.30 g, 12.5 mmol) were added and heating at 80° C. was continued. After 8 h., the reaction was cooled and partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20) to give the desired product (0.14 g, 0.33 mmol, 66%).

후처리

  1. temperatureheating at 80° C.
  2. temperaturethe reaction was cooled
  3. custompartitioned between water and ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

출처 및 근거

ORD 기록
ord-542e11faf0c04255953d092e54cc0035
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091234B2

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