Thionyl Chloride → 3-(chloromethyl)-2-(1-cyclopentyl-1H-pyrazol-5-yl)pyridine hydrochloride

HRID 1484771Notes

Reaction equation

HRID 1484771 reaction equation
[CH:1]1([N:6]2[C:10]([C:11]3[C:16]([CH2:17]O)=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:21]>C(Cl)Cl>[ClH:21].[Cl:21][CH2:17][C:16]1[C:11]([C:10]2[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:7]=[CH:8][CH:9]=2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 90418596(2-(1-cyclopentyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol

Product 1

HCID 904186163-(chloromethyl)-2-(1-cyclopentyl-1H-pyrazol-5-yl)pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(1-cyclopentyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol (301 mg, 1.24 mmol) in DCM (3 mL) was added SOCl2 (3 eq) at 0° C. The reaction mixture was stirred at RT for 15 mins (thew reaction was done in 10 mins by LCMS) 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-cyclopentyl-1H-pyrazol-5-yl)pyridine hydrochloride (305 mg) as an off-white solid, which was used for next step without further purification. MS (ESI) m/z 262.2 [M+H]+.

Workup

  1. waitwas done in 10 mins by LCMS
  2. concentration) and concentrated to dryness
  3. concentrationconcentrated to dryness
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d813c4b7fb6940b1b2e97f84cf37ead7
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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