Sodium Carbonate → HCID 66761510, 화합물

HRID 561834

반응식

HRID 561834 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12](Cl)[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:15][O:16][CH2:17]/[CH:18]=[CH:19]/B1OC(C)(C)C(C)(C)O1.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:34]=CC=C[CH:30]=1.[C:48](=O)([O-])[O-:49].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:11]=[C:12](/[CH:30]=[CH:29]/[CH2:34][O:49][CH3:48])[N:13]=[C:2](/[CH:19]=[CH:18]/[CH2:17][O:16][CH3:15])[CH:3]=2)[CH2:10][CH2:9]1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 215100262,6-Dichloro-N-cyclopropylisonicotinamide

생성물 1

HCID 66761510HCID 66761510, 화합물

시약·촉매·용매 2

HCID 83469Palladium bromide (PdBr2)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 2,6-dichloro-N-cyclopropylisonicotinamide from Amine 41, Step 1 (I eq.) in DMF (0.08 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.7 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 5 eq.). The resulting suspension was heated at 100° C. for 8 h. The reaction mixture was quenched with water and extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a red oil. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  4. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
  5. customafforded the crude product as a red oil
  6. customPurification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-577ce0bfa216420d91f2772d3771d42c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063105B2

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