5-Bromopyridine-2-carboxylic acid → 2-(Azetidin-1-ylcarbonyl)-5-bromopyridine

HRID 1177144Notes

Reaction equation

HRID 1177144 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][N:6]=1)=[O:4].Br[C:14]1C=CC(C(O)=O)=NC=1.Cl.N1CCC1>>[N:2]1([C:3]([C:5]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][N:6]=2)=[O:4])[CH2:12][CH2:14][CH2:1]1

Participants

4

Reactant 3

HCID 6085445-Bromopyridine-2-carboxylic acidHCID 12308726Azetidine hydrochlorideHCID 228316185-bromo-N,N-dimethylpicolinamide

Product 1

HCID 536296172-(Azetidin-1-ylcarbonyl)-5-bromopyridine

Procedure

The title compound was prepared in a similar manner as described for Intermediate 161a, from 5-bromopyridine-2-carboxylic acid (1.50 g, 7.43 mmol) and azetidine hydrochloride (954 mg, 10.2 mmol) to give a yellow solid (1.38 g, 77% yield). 1H NMR (400 MHz, CDCl3) δ 8.58 (d, J=2.02 Hz, 1 H) 7.93-7.99 (m, 1 H) 7.90 (d, J=2.27 Hz, 1 H) 4.65 (t, J=7.71 Hz, 2 H) 4.20 (dd, J=8.34, 7.33 Hz, 2 H) 2.27-2.36 (m, 2 H); LCMS for C9HgBrN2O m/z 241.00 (M+H)+.

Sources & evidence

ORD record
ord-edf0328181c3473192fa0649d3c8c58a
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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