Dimethylformamide → Methyl 3-{[5-(5-formylpyrazin-2-yl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate

HRID 623903ノート

反応式

HRID 623903 の反応式
CN(C)C=O.Cl[C:7]1[N:8]=[CH:9][C:10]([CH:13]=[O:14])=[N:11][CH:12]=1.[CH3:15][C:16]([CH3:39])([CH2:21][O:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]=1)[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[CH:13]([C:10]1[N:11]=[CH:12][C:7]([C:26]2[C:27]([CH3:29])=[CH:28][C:23]([O:22][CH2:21][C:16]([CH3:15])([CH3:39])[C:17]([O:19][CH3:20])=[O:18])=[N:24][CH:25]=2)=[N:8][CH:9]=1)=[O:14]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 216980675-Chloropyrazine-2-carbaldehydeHCID 67975267Methyl 2,2-dimethyl-3-((4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl)oxy)propanoate

生成物 1

HCID 86698176Methyl 3-{[5-(5-formylpyrazin-2-yl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate収率 74%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

N,N-dimethylformamide (10 mL) was added to 5-chloropyrazine-2-carbaldehyde (500 mg), methyl 2,2-dimethyl-3-{[4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}propanoate (1410 mg) and 2N aqueous sodium carbonate solution (5.26 mL), and after replacing the atmosphere with nitrogen, palladium chloride (dppf) methylene chloride complex (143 mg) was added to the mixture and the resulting mixture was stirred at 65° C. for 2 hours. To the reaction mixture were added ethyl acetate and water, and the liquids were separated. After filtration with Celite, the organic layer was separated, washed with water and then with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 70:30) to obtain methyl 3-{[5-(5-formylpyrazin-2-yl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate (855 mg).

後処理

  1. additionwas added to the mixture
  2. customthe liquids were separated
  3. filtrationAfter filtration with Celite
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialwith a saturated brine, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 70:30)

出典と根拠

ORDレコード
ord-d674b7f94799496d94a50e7428a47345
出典データセット
uspto-grants-2016_04
特許番号
US09302996B2

反応ノート

読み込み中…