Dichloromethane → 5-Bromo-2-(pyrrolidin-1-yl)pyridine

HRID 747791Notes

Reaction equation

HRID 747791 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:19][CH2:20][CH2:21][CH2:22]Br.ClCCl>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 80561,4-DibromobutaneHCID 706222-Amino-5-bromopyridineHCID 81531Diisopropylethylamine

Product 1

HCID 164142265-Bromo-2-(pyrrolidin-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

4.95 g (28.6 mmol) of 2-amino-5-bromopyridine was dissolved in 40 ml of toluene. 9.95 ml (57.2 mmol) of diisopropylethylamine, 6.15 g (28.6 mmol) of 1,4-dibromobutane and 100 mg (0.82 mmol) of 4-(dimethylamino)pyridine were added to the solution, and they were stirred for three nights. After the treatment with dichloromethane as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-ffc62eb2a6a84a6f950a68a81426d2dc
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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