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

HRID 861045노트

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HRID 861045 반응식
[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

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 5462224MagnesiumHCID 22037579HCID 22037579, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

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 C22H18N2OF.0.6EtOAC: C, 71.1; H, 5.6; N, 10.2; Found: C, 70.9; H, 5.47; N, 10.2.

후처리

  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

출처 및 근거

ORD 기록
ord-89531dbdd07a46c9b977d5da6dd09149
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153959B2

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