4-(2-Methoxy-2-oxoethyl)benzylboronic Acid Pinacol Ester → HCID 90338586, compound

HRID 1509021Notes

Reaction equation

HRID 1509021 reaction equation
FC(F)(F)S(O[C:7]1[C:8]2[S:23](=[O:25])(=[O:24])[CH2:22][CH2:21][CH2:20][C:9]=2[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[N:12]=1)(=O)=O.CC1(C)C(C)(C)OB([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([CH2:43][C:44]([O:46][CH3:47])=[O:45])=[CH:39][CH:38]=2)O1>>[Cl:19][C:15]1[CH:14]=[C:13]([C:11]2[N:12]=[C:7]([CH2:36][C:37]3[CH:38]=[CH:39][C:40]([CH2:43][C:44]([O:46][CH3:47])=[O:45])=[CH:41][CH:42]=3)[C:8]3[S:23](=[O:25])(=[O:24])[CH2:22][CH2:21][CH2:20][C:9]=3[N:10]=2)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 674944814-(2-Methoxy-2-oxoethyl)benzylboronic Acid Pinacol EsterHCID 90111594HCID 90111594, compound

Product 1

HCID 90338586HCID 90338586, compoundYield 22.7%

Procedure

Following general procedure H, 2-(3-chlorophenyl)-5,5-dioxido-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl trifluoromethanesulfonate (0.250 g, 0.56 mmol) was reacted with methyl 2-(4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)phenyl)acetate (0.160 g, 0.56 mmol) to afford the title compound (0.058 g, 22%) as a white solid. MW=456.9. 1H NMR (CDCl3, 500 MHz) δ 8.28 (t, J=1.2 Hz, 1H), 8.30-8.26 (m, 1H), 7.52-7.45 (m, 3H), 7.42-7.37 (m, 1H), 7.23 (d, J=8.0 Hz, 2H), 4.60 (s, 2H), 3.67 (s, 3H), 3.60 (s, 2H), 3.50-3.45 (m, 2H), 3.18 (t, J=6.5 Hz, 2H), 2.54-2.48 (m, 2H); APCI MS m/z 457 [M+H]+.

Sources & evidence

ORD record
ord-ae080a28b6e246ca955a835ae2a36c79
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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