Potassium Carbonate → 1-(methoxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2366884ノート

反応式

HRID 2366884 の反応式
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[CH3:15][O:16][CH2:17]I.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:15][O:16][CH2:17][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 139376Iodomethyl methyl etherHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 671939951-(methoxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole収率 52.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
35 °C

実験手順

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (10.00 g, 51.5 mmol) was dissolved in acetonitrile (40 mL) and stirred at 35° C. for 5 min under nitrogen atmosphere then cooled to room temperature. Iodomethyl methyl ether (21.83 mL, 258 mmol) and potassium carbonate (35.6 g, 258 mmol) were added and the resulting mixture was stirred at 35° C. for 3 h then cooled to room temperature. The insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and the organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 100 G silica cartridge (gradient: 0 to 50% AcOEt in hexanes) gave 1-[(methyloxy)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (6.45 g, 50% pure by LCMS, 26%) as a yellow liquid which was used in the next step without further purification.

後処理

  1. temperaturethen cooled to room temperature
  2. stirringthe resulting mixture was stirred at 35° C. for 3 h
  3. temperaturethen cooled to room temperature
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. washthe organic phase was washed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue by SP4

出典と根拠

ORDレコード
ord-a0c8673b16564f298e54b7e6561851b5
出典データセット
uspto-grants-2014_04
特許番号
US08697725B2

反応ノート

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