10-bromo-3-iodo-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carb oxamide → tert-butyl 3-(10-bromo-2-carbamoyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepin-3-yl)azetidine-1-carboxylate

HRID 575475Notes

Reaction equation

HRID 575475 reaction equation
[Br:1][C:2]1[C:3](F)=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:19]4[CH2:21][CH2:20]4)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:22]=1.BrC1C=CC2C3CC(C3)N3C(I)=C(C(N)=O)N=C3C=2C=1.[I-].[C:45]([O:49][C:50]([N:52]1CC([Zn+])C1)=[O:51])([CH3:48])([CH3:47])[CH3:46]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:10][CH:9]([CH2:12]3)[N:8]3[C:13]([CH:19]4[CH2:20][N:52]([C:50]([O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:51])[CH2:21]4)=[C:14]([C:16](=[O:17])[NH2:18])[N:15]=[C:7]3[C:6]=2[CH:22]=1

Participants

4

Reactant 3

HCID 8669336510-bromo-3-iodo-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carb oxamideHCID 8669353710-bromo-3-cyclopropyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamideHCID 178452187HCID 178452187, compound

Product 1

HCID 86693543tert-butyl 3-(10-bromo-2-carbamoyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepin-3-yl)azetidine-1-carboxylate

Procedure

Similar to as described for 10-bromo-3-cyclopropyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide above, 10-bromo-3-iodo-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was coupled with (1-(tert-butoxycarbonyl)azetidin-3-yl)zinc(II) iodide to give the titled compound after purification by flash column chromatography.

Sources & evidence

ORD record
ord-56e34bc0e53f4faca690bbbe62337c40
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…