Potassium Carbonate → Methyl 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxylate

HRID 729451Notes

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Cl[C:17]1[N:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[N:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:17]2[N:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[N:21][CH:22]=2)[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(2-bromo-5-fluorophenoxy)piperidine from Step 2 (1.90 g, 6.95 mmol), methyl 5-chloropyrazine-2-carboxylate (1.00 g, 5.79 mmol) and potassium carbonate (1.60 g, 11.59 mmol) in dioxane (30 mL) was heated at 100° C. After a period of 2 h, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The solvent was separated, dried over sodium sulfate and evaporated. The title compound was purified by flash chromatography (50% ethyl acetate in hexane) to provide the title compound.

Workup

customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
customThe solvent was separated
dry with materialdried over sodium sulfate
customevaporated
customThe title compound was purified by flash chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-62fbe6e62f1a452e8b80e3f3572ea715
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582633B2

Reaction notes

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