Imidazole → Methyl 5-bromopyridine-3-carboxylate

HRID 1790386Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.N1C=CN=C1.C([Si](C)(C)Cl)(C)(C)C.CN(C)[CH:25]=[O:26]>>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:3]=1)[C:8]([O:26][CH3:25])=[O:9]

Participants

Reactant 4

HCID 795Imidazole

HCID 6228Dimethylformamide

HCID 28928tert-Butyldimethylsilyl chloride

HCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 699336Methyl 5-bromopyridine-3-carboxylate

Procedure

5-Bromo-3-hydroxymethylpyridine (3.41 g), imidazole (13.33 g), t-butyldimethylchlorosilane (13.57 g) and N,N-dimethylformamide (63 ml) were treated as reported in J. Am. Chem. Soc., 6190 (1972) to give the title compound (5.605 g) as a yellow oil (yield: quantitative).

Sources & evidence

ORD record: ord-a6a5d351b07140b0b4919059e391a22c
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071201B2

Reaction notes

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