Dibromomethane → 2-Bromo-1-(5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazol-3-yl)ethan-1-one

HRID 8083

反応式

HRID 8083 の反応式
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:12]=[C:11]([C:20]([O:22]C)=O)[CH:10]=2)=[CH:5][CH:4]=1.[Br:24][CH2:25]Br.C[Li]>C1COCC1>[Br:24][CH2:25][C:20]([C:11]1[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=2)[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:12]=1)=[O:22]

参加物

5

反応物 3

HCID 3024DibromomethaneHCID 68818768Methyl 5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazole-3-carboxylateHCID 178418348HCID 178418348、化合物

生成物 1

HCID 875873542-Bromo-1-(5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazol-3-yl)ethan-1-one収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of methyl 5-(4-methylthiophenyl)-1-(2-pyridyl)pyrazole-3-carboxylate (prepared as described in Penning, T. D. et al. J. Med. Chem. 1997, 40, 1347–1365.; 0.39 g, 1.2 mmol) and dibromomethane (0.17 mL, 2.4 mmol) in THF (10 mL) at −78° C. under nitrogen atmosphere was added methyllithium (1.6 M in ether, 1.4 mL, 2.2 mmol). After being stirred at the same temperature for 90 minutes, the solution was quenched with aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Chromatography of the residue on silica gel (2:1 EtOAc:hexane) gave the title compound (0.32 g, 69% yield) as a white foam. 1H NMR (300 MHz, CDCl3) δ 8.42–8.40 (m, 1H), 7.83 (m, 1H), 7.55–7.51 (m, 1H), 7.17–7.09 (m, 4H), 7.02 (s, 1H), 4.70 (s, 2H), 2.46 (s, 3H); LRMS (API-TIS) m/z 388 and 390 (MH+).

後処理

  1. customthe solution was quenched with aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-71614f4ee7974ddbb313fb7d2c4b05c4
出典データセット
uspto-grants-2006_08
特許番号
US07087630B2

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