Hydrochloric Acid → 2-fluoro-4-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 1788139노트

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HRID 1788139 반응식
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6](CN)=[C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:4]=1.FC1C=CC([C:21]#[N:22])=C(N2C=NC=N2)C=1.Cl>C(O)C.[Pd]>[N:11]1([C:5]2[CH:6]=[CH:7][C:8]([C:21]#[N:22])=[C:3]([F:2])[CH:4]=2)[CH:15]=[N:14][CH:13]=[N:12]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 210698804-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrileHCID 21069882(4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride

생성물 1

HCID 210698712-fluoro-4-(1H-1,2,4-triazol-1-yl)benzonitrile수율 99%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

(4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride). Intermediate 67, 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile, (2.46 g, 13.13 mmol) was dissolved in hot ethanol (150 mL). To this was added 1N HCl (15 mL) followed by 10% Pd—C (200 mg). The mixture was treated with H2 at 55 psi for 4 h in a Parr shaker then filtered over Celite and the solvent removed under reduced pressure. The resulting residue was partitioned between ethyl acetate and water. The aqueous phase was separated and lyophilized to afford the title compound as a white powder (2.96 g, 99% yield). 1H NMR (500 MHz, CD3OD) δ ppm: 9.51 (1H, s), 8.63 (1H, s), 7.85 (1H, dd, J=8.5, 5.8 Hz), 7.68 (1H, dd, J=8.8, 2.4 Hz), 7.49 (1H, td, J=8.3, 2.4 Hz), 4.20 (2H, s). LCMS (M+H) calcd for C9H10N4F: 193.08; found: 193.16.

후처리

  1. additionThe mixture was treated with H2 at 55 psi for 4 h in a Parr shaker
  2. filtrationthen filtered over Celite
  3. customthe solvent removed under reduced pressure
  4. customThe resulting residue was partitioned between ethyl acetate and water
  5. customThe aqueous phase was separated

출처 및 근거

ORD 기록
ord-ea34a7e330bd406f98bf6c5b058cab7f
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07511037B2

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