1,2-Dibromoethane → HCID 58204752, compound

HRID 886022Notes

Reaction equation

HRID 886022 reaction equation
Cl.Cl.[Cl:3][C:4]1[N:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)[CH:5]=1.Br[CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:3][C:4]1[N:9]=[CH:8][C:7]2[O:10][CH2:18][CH2:17][N:15]3[CH:14]=[CH:13][N:12]=[C:11]3[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 136374306HCID 136374306, compound

Product 1

HCID 58204752HCID 58204752, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.30 g (8.55 mmol) of 6-chloro-4-(1H-imidazol-2-yl)pyridin-3-ol dihydrochloride, 1,2-dibromoethane (1.842 mL, 21.37 mmol) and Cesium Carbonate (19.46 g, 59.74 mmol) in 120 ml of N,N-Dimethylformamide was heated for 3 hours at 90° C. The mixture was filtered and concentrated in high vacuum to give 10-Chloro-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine. Weight 1.88 g (99%) MS (ESI+): 222.2. 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.17 (s, 1H), 7.24 (d, J=1.0, 1H), 7.10 (d, J=0.9, 1H), 4.51-4.45 (m, 4H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in high vacuum

Sources & evidence

ORD record
ord-024ef420f4bf426aaf98559fd2e3b9bd
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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