3,4-Difluorobenzeneboronic acid → CID 23571065

HRID 1180633Notes

Reaction equation

HRID 1180633 reaction equation
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[F:7][C:8]1[CH:9]=[C:10](B(O)O)[CH:11]=[CH:12][C:13]=1[F:14].CC1(C)C(C)(C)OB([C:26]2[CH:27]=[CH:28][C:29]3[CH2:36][C@H:35]4[C@:37]5([CH2:41][N:40]([CH2:42][C:43]([F:46])([F:45])[F:44])[S:39](=[O:48])(=[O:47])[NH:38]5)[C@H:32]([CH2:33][CH2:34]4)[CH2:31][C:30]=3[CH:49]=2)O1>>[F:7][C:8]1[CH:9]=[C:10]([N:5]2[CH:6]=[C:2]([C:26]3[CH:27]=[CH:28][C:29]4[CH2:36][C@H:35]5[C@:37]6([CH2:41][N:40]([CH2:42][C:43]([F:46])([F:45])[F:44])[S:39](=[O:47])(=[O:48])[NH:38]6)[C@H:32]([CH2:33][CH2:34]5)[CH2:31][C:30]=4[CH:49]=3)[N:3]=[CH:4]2)[CH:11]=[CH:12][C:13]=1[F:14]

Participants

4

Reactant 3

HCID 27343373,4-Difluorobenzeneboronic 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 23571065CID 23571065

Procedure

Prepared from 4-bromo-1H-imidazole, 3,4-difluorophenylboronic acid and homochiral boronate from Example 24 Step 1 following the procedures in Example 76 Steps 1 and 2. □ (1H, 400 MHz, CDCl3) 1.18-1.24 (2H, m), 1.70-1.73 (2H, m), 2.43-2.49 (2H, m), 2.69-2.81 (2H, m), 3.20-3.26 (2H, m), 3.44 (2H, s), 3.68 (2H, q, J=8.7 Hz), 4.72 (1H, s), 7.13 (1H, d, J=7.8 Hz), 7.19-7.22 (1H, m) 7.28-7.35 (2H, m), 7.48 (1H, d, J=1 Hz), 7.54 (1H, dd, J=7.7, 2 Hz), 7.61 (1H, s), 7.83 (1H, d, J=1 Hz). MS (ES+) 539 ([MH]+).

Sources & evidence

ORD record
ord-0fe1f10fc1dc4a209134969ea886d436
Source dataset
uspto-grants-2007_10
Patent number
US07282513B2

Reaction notes

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