3-Fluorophenylboronic acid → CID 23571066

HRID 1180636Notes

Reaction equation

HRID 1180636 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][CH:13]=1.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:9]=[C:10]([N:5]2[CH:6]=[C:2]([C:25]3[CH:26]=[CH:27][C:28]4[CH2:35][C@H:34]5[C@:36]6([CH2:40][N:39]([CH2:41][C:42]([F:45])([F:44])[F:43])[S:38](=[O:46])(=[O:47])[NH:37]6)[C@H:31]([CH2:32][CH2:33]5)[CH2:30][C:29]=4[CH:48]=3)[N:3]=[CH:4]2)[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 27339863-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 23571066CID 23571066

Procedure

Prepared from 4-bromo-1H-imidazole, 3-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) 1.33-1.43 (2H, m), 1.69-1.73 (2H, m), 2.45-2.48 (2H, m), 2.68-2.82 (2H, m), 3.20-3.26 (2H, m), 3.44 (2H, s), 3.68 (2H, q, J=8.7 Hz), 4.75 (1H, s), 7.07-7.20 (3H, m), 7.24 (1H, s), 7.45-7.56 (3H, m), 7.61 (1H, s), 7.89 (1H, s). MS (ES+) 521 ([MH]+).

Sources & evidence

ORD record
ord-2ac67b0a366546539ad3893078bf054b
Source dataset
uspto-grants-2007_10
Patent number
US07282513B2

Reaction notes

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