2-Furancarbonyl chloride → HCID 58526528, compound

HRID 522503Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Li+].[Cl-].C([Cu])#N.[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](Cl)=[O:20]>C1COCC1>[Cl:1][C:2]1[C:7]([C:19]([C:15]2[O:14][CH:18]=[CH:17][CH:16]=2)=[O:20])=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

4,6-Dichloropyrimidine 6 (149 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 45 min according to TP 2. CuCN.2LiCl (1.0 M solution in THF, 1.1 mL, 1.1 mmol) was slowly added at −20° C. and the reaction mixture was stirred at the same temperature for 30 min. Then, furan-2-carbonyl chloride (261 mg, 2.0 mmol) was dropwise added at −20° C. and the resulting mixture was allowed to warm up slowly to 25° C. overnight. The reaction mixture was quenched with a sat. aq. NH4Cl solution (30 mL), extracted with diethyl ether (5×30 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane 1:1) furnished 8b as a colourless solid (172 mg, 71%).

Workup

customThe reaction mixture was quenched with a sat. aq. NH4Cl solution (30 mL)
extractionextracted with diethyl ether (5×30 mL)
dry with materialdried over anhydrous Na2SO4
filtrationAfter filtration
customthe solvent was evaporated in vacuo
customPurification by flash-chromatography (CH2Cl2/n-pentane 1:1)

Sources & evidence

ORD record: ord-4d488838323f4555a4e464aa7d882f50
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334237B2

Reaction notes

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