Ethylene carbonate → HCID 58204827, compound

HRID 1629409Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:6][CH:5]=[C:4]([Cl:13])[N:3]=1.C1(=O)O[CH2:17][CH2:16][O:15]1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:13][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:9]([CH:10]=[CH:11][N:12]=3)[CH2:17][CH2:16][O:15][C:2]=2[N:3]=1

Participants

Reactant 3

HCID 7303Ethylene carbonate

HCID 10796Cesium carbonate

HCID 86652308HCID 86652308, compound

Product 1

HCID 58204827HCID 58204827, compound

Conditions

Temperature: 90 °C

Procedure

A mixture of 0.856 g (4.00 mmol) of 2,6-dichloro-3-(1H-imidazol-2-yl)pyridine, 704 mg (8.00 mmol) of ethylene carbonate and 2930 mg (9.00 mmol) of cesium carbonate was heated in 25.0 ml of N,N-dimethylformamidefor 13 hours at 90° C. The mixture was filtered, the filtrate concentrated in high vacuum, the residue purified on 10 g of silica column eluting with 80% of ethyl acetate in heptane to give 9-chloro-5,6-dihydroimidazo[1,2-d]pyrido[3,2-f][1,4]oxazepine. Yield 0.359 g (41%). M/z 222.0, calc. 221.04. 1H NMR (500 MHz, CDCl3) δ 8.84 (d, J=8.2, 1H), 7.18 (s, 1H), 7.15 (d, J=8.2, 1H), 7.02 (s, 1H), 4.63-4.57 (m, 2H), 4.47-4.41 (m, 2H)

Workup

filtrationThe mixture was filtered
concentrationthe filtrate concentrated in high vacuum
customthe residue purified on 10 g of silica column
washeluting with 80% of ethyl acetate in heptane

Sources & evidence

ORD record: ord-8b73852dda6f46eeb53d5347828a56f3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785626B2

Reaction notes

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