Potassium Carbonate → HCID 53629688, compound

HRID 1011815Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@@H:13]([CH3:16])[CH2:14][OH:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N:17]1([C:21]([C:23]2[CH:24]=[C:25]([Cl:30])[C:26](Cl)=[N:27][CH:28]=2)=[O:22])[CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:17]1([C:21]([C:23]2[CH:24]=[C:25]([Cl:30])[C:26]([O:1][C:2]3[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@@H:13]([CH3:16])[CH2:14][OH:15])[CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])=[N:27][CH:28]=2)=[O:22])[CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate (2.35 g, 10.39 mmol), 5-(azetidin-1-ylcarbonyl)-2,3-dichloropyridine (2.41 g, 10.39 mmol) and potassium carbonate (2.87 g, 20.8 mmol) in acetonitrile (20 mL) was stirred in a microwave reactor at 160° C. for 6 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo. The crude oil was chromatographed on silica, eluting with 30-100% ethyl acetate in isohexane, to give the desired compound as a yellow oil (5.3 g).

Workup

customThe solvent was removed in vacuo
customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
washThe organic layer was washed with brine (50 mL)
dry with materialdried (MgSO4)
customthe solvent removed in vacuo
customThe crude oil was chromatographed on silica
washeluting with 30-100% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-0b3e55eb32ea423cb31babffbc68bc7a
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977328B2

Reaction notes

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