Dimethylformamide → 1-(4-Bromo-3-(trifluoromethyl)-1H-pyrazol-1-YL)-2-methylpropan-2-OL

HRID 2095657ノート

反応式

HRID 2095657 の反応式
[Br:1][C:2]1[C:3]([C:7]([F:10])([F:9])[F:8])=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH3:22][C:23]1([CH3:26])[CH2:25][O:24]1>>[Br:1][C:2]1[C:3]([C:7]([F:10])([F:9])[F:8])=[N:4][N:5]([CH2:22][C:23]([CH3:26])([OH:24])[CH3:25])[CH:6]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 178506296HCID 178506296、化合物

生成物 1

HCID 670045921-(4-Bromo-3-(trifluoromethyl)-1H-pyrazol-1-YL)-2-methylpropan-2-OL

反応条件

温度
90 °C

実験手順

To a mixture of 4-bromo-3-trifluoromethyl-1H-pyrazole (200.0 mg, 0.9304 mmol), K2CO3 (200.0 mg, 1.447 mmol) and DMF (3 mL, 40 mmol) was added 2,2-dimethyloxirane (0.5 mL, 6 mmol), and the mixture was heated to 90° C. for 2 h in a sealed tube. The material was transferred to a separation funnel, extracting with EtOAc and washing with water (3×). The organic layer was loaded onto silica gel for column chromatography, eluting with 10-30% EtOAc/heptane. The fractions containing the 3-trifluoromethyl product were concentrated in vacuo to afford the title compound as a brown oil. 1H NMR (400 MHz, CD3OD): δ=1.17 (s, 6H), 4.13 (s, 2H), 7.87 (s, 1H). MS (ES+): m/z=287.00/289.00 (100/100) [MH+]. HPLC: tR=1.35 min (polar—3 min, UPLC-ACQUITY).

後処理

  1. customThe material was transferred to a separation funnel
  2. extractionextracting with EtOAc
  3. washwashing with water (3×)
  4. washeluting with 10-30% EtOAc/heptane
  5. additionThe fractions containing the 3-trifluoromethyl product
  6. concentrationwere concentrated in vacuo

出典と根拠

ORDレコード
ord-5623af810b904d7084714d3251798ef5
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

読み込み中…