2,4-Difluorophenylboronic acid → CID 23571062

HRID 1180635Notes

Reaction equation

HRID 1180635 reaction equation
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1B(O)O.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:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N:5]1[CH:6]=[C:2]([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:47])(=[O:48])[NH:38]5)[C@H:32]([CH2:33][CH2:34]4)[CH2:31][C:30]=3[CH:49]=2)[N:3]=[CH:4]1

Participants

4

Reactant 3

HCID 27343342,4-Difluorophenylboronic 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 23571062CID 23571062

Procedure

Prepared from 4-bromo-1H-imidazole, 2,4-difluorophenylboronic acid and homochiral boronate from Example 24 Step 1 following the procedures in Example 76 Steps 1 and 2. δ (1H, 360 MHz, CDCl3) 1.20-1.27 (2H, m), 1.69-1.73 (2H, m), 2.45-2.47 (2H, m), 2.68-2.82 (2H, m), 3.20-3.26 (2H, m), 3.43 (2H, s), 3.68 (2H, q, J=8.7 Hz), 4.71 (1H, s), 7.00-7.13 (3H, m), 7.40-7.45 (2H, m), 7.54 (1H, d, J=7.9 Hz), 7.61 (1H, s), 7.78 (1H, s). MS (ES+) 539 ([MH]+).

Sources & evidence

ORD record
ord-af37e7924cb84626ace001f3ecc1675b
Source dataset
uspto-grants-2007_10
Patent number
US07282513B2

Reaction notes

Loading…