Methyl 5-bromo-6-(2,2,2-trifluoroethoxy)nicotinate → Methyl 5-ethyl-6-(2,2,2-trifluoroethoxy)nicotinate

HRID 623503Notes

Reaction equation

HRID 623503 reaction equation
Br[C:2]1[C:3]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:18]([Zn]CC)[CH3:19]>>[CH2:18]([C:2]1[C:3]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:19]

Participants

3

Reactant 2

HCID 66686828Methyl 5-bromo-6-(2,2,2-trifluoroethoxy)nicotinateHCID 178418750HCID 178418750, compound

Product 1

HCID 67510225Methyl 5-ethyl-6-(2,2,2-trifluoroethoxy)nicotinateYield 73%

Procedure

The title compound is prepared in 73% yield (610 mg, a white solid) from methyl 5-bromo-6-(2,2,2-trifluoroethoxy)nicotinate (1.0 g, 3.2 mmol, Step-1) and diethylzinc (6.4 mL, 6.4 mmol, 1M solution in n-hexane) instead of dimethylzinc by the similar manner in Step-3 of Amine-27.

Sources & evidence

ORD record
ord-3c98c2ce92a1408b9ce8eff33afa6f27
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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