Toluene → 3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine

HRID 2408181Notes

Reaction equation

HRID 2408181 reaction equation
[Cl:1][C:2]1[C:6]([NH:7]C(=O)OC(C)(C)C)=[CH:5][N:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:3]=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[Cl:1][C:2]1[C:6]([NH2:7])=[CH:5][N:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 69259655HCID 69259655, compound

Product 1

HCID 674993943-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amineYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (2 g, 6.79 mmol) in dichloromethane (6.79 ml) was added trifluoroacetic acid (6.79 ml) and the mixture was left stirring at room temperature for 2 hours. Toluene (12 mL) was added and the reaction was concentrated to near dryness. The mixture was poured into a separatory funnel containing saturated aqueous sodium bicarbonated and was extracted with dichloromethane. The combined organic layers were concentrated to give 3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.954 g, 4.90 mmol, 72.2%) as a white solid: mp 137.9-139.9° C.; 1H NMR (400 MHz, CDCl3) δ 8.84 (d, J=2.4 Hz, 1H), 8.50 (dd, J=4.7, 1.4 Hz, 1H), 7.95 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.52 (s, 1H), 7.37 (ddd, J=8.4, 4.7, 0.7 Hz, 1H), 3.18 (s, 2H); ESIMS m/z 196 ([M+H]+).

Workup

  1. waitthe mixture was left
  2. concentrationthe reaction was concentrated
  3. additionThe mixture was poured into a separatory funnel
  4. additioncontaining saturated aqueous sodium
  5. extractionwas extracted with dichloromethane
  6. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-9f697f2ad0e64092a3e5ddcc72866178
Source dataset
uspto-grants-2014_08
Patent number
US08815271B2

Reaction notes

Loading…