4-(Trifluoromethyl)phenylboronic acid → [6s,9r,11r] 2',3',4',5,5',6,7,8,9,10-Decahydro-2-(1-(4-(trifluoromethyl)phenyl)-imidazol-4-yl)-5'-(2,2,2-trifluoroethyl)-spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole] 1',1'-dioxide

Participants

Role	Name	HCID	Charge
Reactant	4-(Trifluoromethyl)phenylboronic acid	HCID 2734389	—
Reactant	[6s,9r,11r]2',3',4',5,5',6,7,8,9,10-Decahydro-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-5'-(2,2,2-trifluoroethyl)spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole]1',1'-dioxide	HCID 23571079	—
Reactant	HCID 178418934	HCID 178418934	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	[6s,9r,11r] 2',3',4',5,5',6,7,8,9,10-Decahydro-2-(1-(4-(trifluoromethyl)phenyl)-imidazol-4-yl)-5'-(2,2,2-trifluoroethyl)-spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole] 1',1'-dioxide	HCID 23571071	—

Reaction Steps

Prepared from 4-bromo-1H-imidazole, 4-(trifluoromethyl)phenylboronic acid and homochiral boronate from Example 24 Step 1 following the procedures in Example 76 Steps 1 and 2. δ (1H, 360 MHz, DMSO) 1.08-1.11 (2H, m), 1.67-1.75 (2H, m), 2.35-2.38 (2H, m), 2.56-2.70 (2H, m), 3.15-3.20 (2H, m), 3.46 (2H, s), 4.00-4.05 (2H, m), 7.15 (1H, d, J=7.2 Hz), 7.56-7.62 (2H, m), 7.90-8.05 (4H, m), 8.36 (1H, s), 8.49 (1H, s). MS (ES+) 571 ([MH]+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07282513B2
Source dataset	uspto-grants-2007_10
ORD ID	ord-46bc9a0c74f6463685c6dc2175c41d7b
Source note	uspto-grants-2007_10