Benzaldehyde → 3-(4-fluorophenyl)-1-methyl-alpha-phenyl-4-(4-pyridinyl)-1H-pyrazole-5-methanol

HRID 1167522ノート

反応式

HRID 1167522 の反応式
[Mg].Br[C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:4]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[CH:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[C:4]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:3]([CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[OH:29])[N:7]([CH3:8])[N:6]=2)=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 5462224MagnesiumHCID 22037579HCID 22037579、化合物

生成物 1

HCID 220376773-(4-fluorophenyl)-1-methyl-alpha-phenyl-4-(4-pyridinyl)-1H-pyrazole-5-methanol収率 12%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To solid magnesium (60 mg, 5 mmol) under nitrogen was added a solution of 4-[5-bromo-3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]pyridine (450 mg, 1.35 mmol) (prepared in accordance with Example A-214) in tetrahydrofuran (7 mL). The mixture was heated at 40° C. for 2 hours. Benzaldehyde (1 mL) was added. The mixture was heated to 45° C. for 2 hours. It was quenched with HCl (10 mL, 1N) and washed with ethyl acetate. The aqueous acid layer was basified and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated to give a residue. The residue was purified with a silica gel column to give the title compound (59 mg, 12% yield). MS: m/z=360 (M+1); 1H NMR was consistent with the proposed structure. Anal. Calc'd for C22H18N2FO..6EtOAC: C, 71.1; H, 5.6; N, 10.2; Found: C, 70.9; H, 5.47; N, 10.2.

後処理

  1. temperatureThe mixture was heated to 45° C. for 2 hours
  2. customIt was quenched with HCl (10 mL, 1N)
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified with a silica gel column

出典と根拠

ORDレコード
ord-bfa1b57b6c2f47f3b75d719e8ce7ee95
出典データセット
uspto-grants-2003_09
特許番号
US06617324B1

反応ノート

読み込み中…