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

HRID 1180638Notes

Reaction equation

HRID 1180638 reaction equation
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[F:7][C:8]([F:19])([F:18])[C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[CH:30][C:31]3[CH2:38][C@H:37]4[C@:39]5([CH2:43][N:42]([CH2:44][C:45]([F:48])([F:47])[F:46])[S:41](=[O:50])(=[O:49])[NH:40]5)[C@H:34]([CH2:35][CH2:36]4)[CH2:33][C:32]=3[CH:51]=2)O1>CS(C)=O>[F:7][C:8]([F:19])([F:18])[C:9]1[CH:14]=[CH:13][C:12]([N:5]2[CH:6]=[C:2]([C:28]3[CH:29]=[CH:30][C:31]4[CH2:38][C@H:37]5[C@:39]6([CH2:43][N:42]([CH2:44][C:45]([F:48])([F:47])[F:46])[S:41](=[O:49])(=[O:50])[NH:40]6)[C@H:34]([CH2:35][CH2:36]5)[CH2:33][C:32]=4[CH:51]=3)[N:3]=[CH:4]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 23571079[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'-dioxideHCID 178418934HCID 178418934, compound

Product 1

HCID 23571071[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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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]+).

Sources & evidence

ORD record
ord-46bc9a0c74f6463685c6dc2175c41d7b
Source dataset
uspto-grants-2007_10
Patent number
US07282513B2

Reaction notes

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