Sodium Carbonate → HCID 66761510、化合物

HRID 561834

反応式

HRID 561834 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 66761510HCID 66761510、化合物

試薬・触媒・溶媒 2

HCID 83469Palladium bromide (PdBr2)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-577ce0bfa216420d91f2772d3771d42c
出典データセット
uspto-grants-2011_11
特許番号
US08063105B2

関連ノート

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