Dichloromethane → HCID 89851983, compound

HRID 1746896Notes

Reaction equation

HRID 1746896 reaction equation
O[CH2:2][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[N:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1.[Cl:19]CCl>>[Cl:19][CH2:2][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[N:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 89852607HCID 89852607, compound

Product 1

HCID 89851983HCID 89851983, compoundYield 101.7%

Procedure

To a solution of ethyl 2-(3-(hydroxymethyl)-1H-pyrazol-1-yl)nicotinate (3.76 g, 13.69 mmol) in dichloromethane (100 mL) thionyl chloride (1.1 mL, 15.07 mmol) was added dropwise under stirring. After the reaction was completed, the mixture was concentrated and purified by chromatography over silica gel (eluent CH2Cl2+0-5% methanol) to give 3.7 g of the title compound as clear oil; ESI-MS [M+H]+: 266.1. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.64 (dd, 1H), 8.49 (d, 1H), 8.13 (dd, 1H), 7.53 (dd, 1H), 6.65 (d, 2H), 4.23 (q, 2H), 1.17 (t, 3H).

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by chromatography over silica gel (eluent CH2Cl2+0-5% methanol)

Sources & evidence

ORD record
ord-6eb74b675db046a0aad676d40d8dbcc7
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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