Thionyl Chloride → Pyridine, 3-(chloromethyl)-2-(1-(1-methylethyl)-1H-pyrazol-5-yl)-, hydrochloride (1:2)

HRID 1484769Notes

Reaction equation

HRID 1484769 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[C:14]([CH2:15]O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].O=S(Cl)[Cl:19]>C(Cl)Cl>[ClH:19].[Cl:19][CH2:15][C:14]1[C:9]([C:8]2[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][CH:7]=2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 896547582-(1-(1-Methylethyl)-1H-pyrazol-5-yl)-3-pyridinemethanol

Product 1

HCID 86690720Pyridine, 3-(chloromethyl)-2-(1-(1-methylethyl)-1H-pyrazol-5-yl)-, hydrochloride (1:2)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol) (440 mg, 2.02 mmol) in DCM (4 mL) was added SOCl2 (2 eq) at 0° C. The reaction mixture was stirred at RT for 15 mins and concentrated to dryness. The crude solid was suspended in toluene and concentrated to dryness. The process was repeated three times and dried under vacuum to give 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride (432 mg) as an off-white solid, which was used for next step without further purification. MS (ESI) m/z 236.5 [M+H]+.

Workup

  1. concentrationconcentrated to dryness
  2. concentrationconcentrated to dryness
  3. customdried under vacuum

Sources & evidence

ORD record
ord-ada9ce2e2efb4289b7691829d9d2c6e2
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

Loading…