Pyrrolidine → N-(3-iodo-4-methylphenyl)-2-pyrrolidin-1-yl-isonicotinamide

HRID 31413Notes

Reaction equation

HRID 31413 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][N:14]=[C:13](Cl)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 219145572-Chloro-N-(3-iodo-4-methylphenyl)pyridine-4-carboxamide2×

Product 1

HCID 21914627N-(3-iodo-4-methylphenyl)-2-pyrrolidin-1-yl-isonicotinamide

Procedure

A solution of N-(3-iodo-4-methylphenyl)-2-chloro-isonicotinamide (Intermediate 18) (7.00 g, 18.8 mmol) in pyrrolidine (20 ml) was heated at 80° C. under an atmosphere of nitrogen for 16 hours. Excess pyrrolidine was removed in vacuo and the residue was titurated with diethyl ether (20 ml). The resulting solid was collected by filtration and dried in vacuo to give N-(3-iodo-4-methylphenyl)-2-pyrrolidin-1-yl-isonicotinamide as a pale yellow solid (7.73 g, 18 mmol). LCMS: retention time 2.77 min MH+408. NMR: δH [2H6]—DMSO 10.29 (1H, s), 8.29 (1H, d), 8.20 (1H, d), 7.71 (1H, dd), 7.72 (1H, dd), 6.97 (1H, brd), 6.88 (1H, b), 3.45 (2H, apparent t), 3.09 (2H, m), 2.35 (3H, s), 1.98 (2H, m), 1.82 (2H, m).

Workup

  1. customExcess pyrrolidine was removed in vacuo
  2. filtrationThe resulting solid was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-fe386ef4c5444c7daf9e77bfaf366026
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Reaction notes

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