1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one → US10023592, Example 98

HRID 518322Notes

Reaction equation

HRID 518322 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]1=[O:17].Br[C:19]1[CH:24]=[C:23]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=1[O:29][CH2:30][CH:31]1[CH2:33][CH2:32]1>>[CH:31]1([CH2:30][O:29][C:20]2[CH:19]=[CH:24][C:23]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:22][C:21]=2[C:6]2[CH:5]=[CH:4][C:3](=[O:17])[N:2]([CH3:1])[CH:7]=2)[CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 454801941-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 1180216932-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzene

Product 1

HCID 118022228US10023592, Example 98

Procedure

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one was treated with 2-bromo-1-(cyclopropylmethoxy)-4-methylsulfonylbenzene in a manner similar to Example 94 to give the title compound. 1H NMR (CDCl3, 400 MHz): δ 7.86 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.81 (d, J=2.0 Hz, 1H), 7.68-765 (m, 2H), 7.03 (d, J=8.4 Hz, 1H), 6.66 (d, J=8.8 Hz, 1H), 3.95 (d, J=6.8 Hz, 2H), 3.64 (s, 3H), 3.07 (s, 3H), 1.28-1.25 (m, 1H), 0.69-0.65 (m, 2H), 0.34-0.38 (m, 2H). LCMS (M+H)+ 334.

Sources & evidence

ORD record
ord-26af580e52f846ec9e7259aceda2f4bb
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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