1-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid → tert-Butyl 2-(5,5-dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate

HRID 1816879Notes

Reaction equation

HRID 1816879 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.B([C:19]1[N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:21]=[CH:22][CH:23]=1)(O)O>>[CH3:13][C:7]1([CH3:14])[C:6]2[CH:15]=[C:2]([C:19]3[N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:21]=[CH:22][CH:23]=3)[CH:3]=[CH:4][C:5]=2[NH:11][C:10](=[O:12])[CH2:9][O:8]1

Participants

3

Reactant 2

HCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 688658147-bromo-5,5-dimethyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 68866427tert-Butyl 2-(5,5-dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate

Procedure

tert-Butyl 2-(5,5-dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate was prepared from 7-bromo-5,5-dimethyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 2-borono-1H-pyrrole-1-carboxylic acid, 1-tert-butyl ester generally according to the procedure described in example 1. 1H-NMR (DMSO-d6) δ 9.96 (s, 1H), 7.32 (m, 1H), 7.23 (m, 1H), 7.15 (d, J=8.24 Hz, 1H), 7.07 (d, J=8.3 Hz, 1H), 6.25 (m, 2H), 4.23 (s, 2H), 1.55 (s, 6H), 1.36 (s, 9H); MS (ES) m/z 357 ([M+H]+, 100%).

Sources & evidence

ORD record
ord-20fdc38743c14c0db2f0dbeb53948ac5
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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