2-Fluorophenylboronic acid → CID 23571063

HRID 1180637Notes

Reaction equation

HRID 1180637 reaction equation
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B(O)O.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[CH:27][C:28]3[CH2:35][C@H:34]4[C@:36]5([CH2:40][N:39]([CH2:41][C:42]([F:45])([F:44])[F:43])[S:38](=[O:47])(=[O:46])[NH:37]5)[C@H:31]([CH2:32][CH2:33]4)[CH2:30][C:29]=3[CH:48]=2)O1>>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:5]1[CH:6]=[C:2]([C:25]2[CH:26]=[CH:27][C:28]3[CH2:35][C@H:34]4[C@:36]5([CH2:40][N:39]([CH2:41][C:42]([F:45])([F:44])[F:43])[S:38](=[O:46])(=[O:47])[NH:37]5)[C@H:31]([CH2:32][CH2:33]4)[CH2:30][C:29]=3[CH:48]=2)[N:3]=[CH:4]1

Participants

4

Reactant 3

HCID 27343542-Fluorophenylboronic 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 23571063CID 23571063

Procedure

Prepared from 4-bromo-1H-imidazole, 2-fluorophenylboronic acid and homochiral boronate from Example 24 Step 1 following the procedures in Example 76 Steps 1 and 2. δ (1H, 360 MHz, CDCl3) 1.92-1.97 (2H, m), 2.26-2.29 (2H, m), 3.01-3.03 (2H, m), 3.29-3.36 (2H, m), 3.76-3.82 (2H, m), 4.00 (2H, s), 4.24 (2H, q, J=8.8 Hz), 5.28 (1H, s), 7.69 (1H, d, J=7.8 Hz), 7.84-7.88 (2H, m), 7.90-7.98 (1H, m), 7.99-8.05 (1H, m), 8.08-8.13 (2H, m), 8.19 (1H, s), 8.42 (1H, s). MS (ES+) 521 ([MH]+).

Sources & evidence

ORD record
ord-f6ba69f519724ec68be375c1992cdd10
Source dataset
uspto-grants-2007_10
Patent number
US07282513B2

Reaction notes

Loading…