2-Methylphenyl boronic acid → HCID 178424222, compound

HRID 271343Notes

Reaction equation

HRID 271343 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19](Br)=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O>>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH3:29])=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 178523818HCID 178523818, compound

Product 1

HCID 178424222HCID 178424222, compound

Procedure

From trans-[4-(2-bromo-3-phenyl-allyloxy)-cyclohexyl]-carbamic acid benzyl ester, and 2-methylphenylboronic acid using the procedure described above for Example 11, Step 4, gave the product as a white crystalline solid: MS (m+1)=456.5; 1H NMR (400 MHz, CDCl3) 7.3 (m, 2H), 7.2 (m, 7H), 7.05 (m, 3H), 6.85 (m, 2H), 6.66 (s 1H), 5.05 (s, 2H), 4.55 (s, 1H), 4.28 (s, 2H), 3.5 (m, 1H), 3.42 (s, 3H), 3.3 (m, 1H), 2.0 (m, 4H), 1.4 (dd, 2H), 1.15 (dd, 2H).

Sources & evidence

ORD record
ord-4b13f2e3370e468f9b1eaf4a8fda5698
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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