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

HRID 2108958Notes

Reaction equation

HRID 2108958 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, 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-47d414de81924327849ede439bd1f87a
Source dataset
uspto-grants-2009_04
Patent number
US07514456B2

Reaction notes

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