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

HRID 1788139

反応式

HRID 1788139 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-ea34a7e330bd406f98bf6c5b058cab7f
出典データセット
uspto-grants-2009_03
特許番号
US07511037B2

関連ノート

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