1,2-Dibromoethane → Methyl 5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxylate

HRID 1498083Notes

Reaction equation

HRID 1498083 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[NH:13][CH:14]=[CH:15][N:16]=1.Br[CH2:18][CH2:19]Br>>[N:16]1[CH:15]=[CH:14][N:13]2[C:12]=1[C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[O:1][CH2:19][CH2:18]2

Participants

3

Reactant 2

HCID 78391,2-DibromoethaneHCID 135742047HCID 135742047, compound

Product 1

HCID 58204321Methyl 5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-10-carboxylateYield 76%

Procedure

Following the procedure in Example 17, methyl 4-hydroxy-3-(1H-imidazol-2-yl)benzoate reacted with 1,2-dibromoethane to give methyl 5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate. Yield 76%. MS(ESI+): 245.0. 1H NMR (400 MHz, CDCl3) δ 9.21 (d, J=2.2, 1H), 7.91 (dd, J=8.6, 2.2, 1H), 7.20 (t, J=4.8, 1H), 7.05 (d, J=8.6, 1H), 7.00 (d, J=0.8, 1H), 4.53-4.48 (m, 2H), 4.43-4.39 (m, 2H), 3.91 (d, J=5.9, 3H).

Sources & evidence

ORD record
ord-ef1cb292e92b465d9917d003be94c81c
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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