Methyl iodide → 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

HRID 877766ノート

反応式

HRID 877766 の反応式
IC.[CH3:3][C:4]1([CH3:18])[C:8]([CH3:10])([CH3:9])[O:7][B:6]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[N:15][CH:16]=2)[O:5]1.[C:19](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:19][N:15]1[CH:16]=[C:11]([B:6]2[O:5][C:4]([CH3:18])([CH3:3])[C:8]([CH3:9])([CH3:10])[O:7]2)[CH:12]=[CH:13][C:14]1=[O:17]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178431084HCID 178431084、化合物

生成物 1

HCID 454801941-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one収率 75.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

Iodomethane (0.283 mL, 4.52 mmol) was added to a mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol (0.500 g, 2.262 mmol) and potassium carbonate (1.563 g, 11.31 mmol) in acetonitrile (10 mL). The reaction vial was sealed and stirred at 50° C. for 16 h. The resulting mixture was filtered to remove the inorganic salt and the filter cake rinsed with ethyl acetate. The filtrate was concentrated, treated with ethyl acetate (20 mL) and dichloromethane (20 mL), and filtered to remove the residual inorganic salt. The filtrate was concentrated and dried under vacuum to give crude 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one as white solid (399.4 mg). This material was used in subsequent Suzuki coupling reactions without further purification. 1H NMR (400 MHz, chloroform-d) δ ppm 7.76 (d, J=2.0 Hz, 1H), 7.60 (dd, J=9.2, 2.0 Hz, 1H), 6.52 (d, J=9.0 Hz, 1H), 3.55 (s, 3H), 1.31 (s, 12H).

後処理

  1. customThe reaction
  2. customvial was sealed
  3. filtrationThe resulting mixture was filtered
  4. customto remove the inorganic salt
  5. washthe filter cake rinsed with ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. additiontreated with ethyl acetate (20 mL) and dichloromethane (20 mL)
  8. filtrationfiltered
  9. customto remove the residual inorganic salt
  10. concentrationThe filtrate was concentrated
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-877459a48b2946cc94a339cabd6cf700
出典データセット
uspto-grants-2015_03
特許番号
US08987268B2

反応ノート

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