Acetic Acid → HCID 86679926, compound

HRID 714044Notes

Reaction equation

HRID 714044 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9]CC)=O.[Li+:13].CC([N-]C(C)C)C.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23].CC(O)=O>C1COCC1>[Br:1][C:2]1[C:12]2[CH2:23][C:22]([C:21]([O:25][CH3:26])=[O:24])=[C:7]([O-:9])[C:6]=2[CH:5]=[N:4][CH:3]=1.[Li+:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7294Methyl AcrylateHCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 86679926HCID 86679926, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 5-bromonicotinate (5 g, 21.7 mmol) in THF (22 mL) was added over a period of 20 min to a solution of LDA (23.9 mmol) [generated from N,N-diisopropylamine (3.41 mL, 23.9 mmol) and n-butyllithium (14.9 mL, 23.9 mmol, 1.6M in hexane) in THF (95 mL)] at −78° C. The resulting dark red solution was stirred for 30 min, then methyl acrylate (4.9 mL, 54.3 mmol) in THF (22 mL) was added over 15 min. The reaction was stirred an additional 1.5 h, then aq. 10% AcOH (43.5 mL, 76.1 mmol) was added (giving a pH of 4-5) and the reaction was allowed to warm to room temperature. Evaporation under reduced pressure afforded the title compound (in 50% purity, determined by 1H-NMR) as dark green amorphous solid. MS: 270.0 (M+H+, 1 Br).

Workup

  1. stirringThe reaction was stirred an additional 1.5 h
  2. customgiving a pH of 4-5) and the reaction
  3. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-e34f88f256f4438485e66c8d646c16db
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

Loading…