Water → 2-(4-Fluorophenyl)-3-iodo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine

HRID 1890257Notes

Reaction equation

HRID 1890257 reaction equation
[I:1]Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1.O>ClCCl>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]([I:1])=[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][N:12]3[N:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24640Iodine chlorideHCID 674383212-(4-Fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine

Product 1

HCID 674380732-(4-Fluorophenyl)-3-iodo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.20 g (13.5 mmol) of iodine monochloride in 5 ml of dichloromethane is added dropwise to a solution of 2.66 g (12.3 mmol) of 2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine in 50 ml of dichloromethane, and the mixture is stirred for 12 h. 100 ml of water are added, and the reaction mixture is extracted with 3×50 ml of dichloromethane. The combined organic phases are dried over MgSO4 and freed from the solvent under reduced pressure. This gives 4.40 g (98%) of the desired product; log P(HCOOH): 3.79; 1H-NMR (MeCN-d3): 7.82 (dd, 2H), 7.18 (dd, 2H), 4.11 (dd, 2H), 2.67 (dd, 2H), 2.06 (m, 2H), 1.94 (m, 2H).

Workup

  1. extractionthe reaction mixture is extracted with 3×50 ml of dichloromethane
  2. dry with materialThe combined organic phases are dried over MgSO4

Sources & evidence

ORD record
ord-fade313a1d974d13a00d3f17f66f330f
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

Loading…