Triethylamine → 1-(3,5-Dibromopyridin-4-yl)pyrrolidine-3-carbonitrile

HRID 1622351Notes

Reaction equation

HRID 1622351 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1Cl.[C:10]([CH:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)#[N:11].C(N(CC)CC)C>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[N:14]1[CH2:15][CH2:16][CH:12]([C:10]#[N:11])[CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8170943,5-Dibromo-4-chloropyridineHCID 22181493Pyrrolidine-3-carbonitrile

Product 1

HCID 452752401-(3,5-Dibromopyridin-4-yl)pyrrolidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C was followed using 3,5-dibromo-4-chloropyridine (71 mg, 0.26 mmol), 3-cyanopyrrolidine (25 mg, 0.26 mmol), NMP (3 mL) and triethylamine (72 μL, 0.52 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 99:1) to furnish the title compound E22 as a white solid (9 mg, 10%), m.p. 159-161° C.; umax (CHCl3)/cm−1 3022, 3008, 1678, 1591, 1446, 1235; m/z (ESI) C10H12Br2N3O requires 347.9342, found [M+H]+ 347.9339.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 99:1)

Sources & evidence

ORD record
ord-046b83ed4fdd41dca89c8f6f8fc41cde
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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