2-oxo-2,3-Dihydrobenzooxazole-5-boronic acid → 5-(2-Chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-3H-benzooxazol-2-one

HRID 2218713Notes

Reaction equation

HRID 2218713 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2.[O:19]=[C:20]1[NH:24][C:23]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:22]=2[O:21]1>>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]2[C:3](=[CH:2][C:26]3[CH:27]=[CH:28][C:22]4[O:21][C:20](=[O:19])[NH:24][C:23]=4[CH:25]=3)[C:4]3[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=3[CH2:6][CH2:7][C:8]=2[CH:13]=1

Participants

3

Reactant 2

HCID 597704982-oxo-2,3-Dihydrobenzooxazole-5-boronic acidHCID 688868195-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 688919215-(2-Chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-3H-benzooxazol-2-one

Procedure

Following procedures essentially as described in Example 219 and using 5-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (200 mg, 0.630 mmol) and 2-oxo-2,3-dihydro-benzooxazole-5-boronic acid (134 mg, 0.750 mmol), provides the title compound. Purify by UV-guided semi-prep reverse-phase HPLC to obtain 14 mg (6%) of the Z-isomer (Example 222(a)) of title compound as a white solid (MS (ES) 391 (M+NH4), 372 (M−H); HPLC shows 94% purity) and 5 mg (2%) of the E-isomer (Example 222(b)) of the title compound as a white solid. MS (ES) 391 (M+NH4), 372 (M−H); HPLC shows 96% purity.

Sources & evidence

ORD record
ord-3967fe5e62734996b832484d2f2667ea
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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