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

HRID 623883ノート

反応式

HRID 623883 の反応式
CN(C)C=O.Br[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([F:15])[CH:8]=1.[CH3:16][C:17]([CH3:40])([CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][N:25]=1)[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([C:27]2[C:28]([CH3:30])=[CH:29][C:24]([O:23][CH2:22][C:17]([CH3:16])([CH3:40])[C:18]([O:20][CH3:21])=[O:19])=[N:25][CH:26]=2)=[CH:8][C:9]=1[F:15])#[N:12]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 7360294-Bromo-2-fluorobenzonitrileHCID 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 67973490Methyl 3-{[5-(4-cyano-3-fluorophenyl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate収率 104.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

N,N-dimethylformamide (30 mL) was added to 4-bromo-2-fluorobenzonitrile (2000 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 (4191 mg) and palladium chloride (dppf) methylene chloride complex (408 mg), and after adding 2N aqueous sodium carbonate solution (15 mL) to the mixture, the atmosphere was replaced with nitrogen and the resulting mixture was stirred at 60° C. for 7 hours. Ethyl acetate and water were added to the reaction mixture, and the liquids were separated. The organic layer was separated, washed with a saturated brine, and the residue obtained by concentrating the mixture under reduced pressure was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20) to obtain methyl 3-{[5-(4-cyano-3-fluorophenyl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate (3587 mg).

後処理

  1. customthe liquids were separated
  2. customThe organic layer was separated
  3. washwashed with a saturated brine
  4. customthe residue obtained
  5. concentrationby concentrating the mixture under reduced pressure
  6. customwas purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20)

出典と根拠

ORDレコード
ord-628a36554cbc4bc5a32b391257ecc054
出典データセット
uspto-grants-2016_04
特許番号
US09302996B2

反応ノート

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