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

HRID 889331Notes

Reaction equation

HRID 889331 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 20) (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 dietheyl 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, l8 mmol). LCMS: retention time 2.77 min MH30 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-bd3ea754627e4ba0a8ac983069e8c478
Source dataset
uspto-grants-2012_08
Patent number
US08252818B2

Reaction notes

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