2-Bromo-1-(cyclopropylmethoxy)-4-(ethylsulfonyl)benzene → US10023592, Example 280

HRID 575760Notes

Reaction equation

HRID 575760 reaction equation
F[C:2]1[C:3](=[O:18])[N:4]([CH3:17])[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.Br[C:20]1[CH:25]=[C:24]([S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[O:31][CH2:32][CH:33]1[CH2:35][CH2:34]1.BrC1C=C(S(C)(=O)=O)C=CC=1OC[CH:49]1[CH2:51][CH2:50]1>>[CH:49]1([C:2]2[C:3](=[O:18])[N:4]([CH3:17])[CH:5]=[C:6]([C:20]3[CH:25]=[C:24]([S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=3[O:31][CH2:32][CH:33]3[CH2:35][CH2:34]3)[CH:7]=2)[CH2:51][CH2:50]1

Participants

4

Reactant 3

HCID 896561482-Bromo-1-(cyclopropylmethoxy)-4-(ethylsulfonyl)benzeneHCID 1180216932-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzeneHCID 1238237903-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one

Product 1

HCID 118022958US10023592, Example 280

Procedure

The title compound was prepared in a manner similar to Example 119, substituting 3-cyclopropyl-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one for 3-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one and 2-bromo-1-(cyclopropylmethoxy)-4-ethylsulfonylbenzene for 2-bromo-1-(cyclopropylmethoxy)-4-methanesulfonylbenzene. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.33-0.41 (m, 2H) 0.55-0.61 (m, 2H) 0.63-0.69 (m, 2H) 0.83-0.91 (m, 2H) 1.07-1.14 (m, 3H) 1.19-1.25 (m, 1H) 2.01-2.12 (m, 1H) 3.23-3.30 (m, 2H) 3.52 (s, 3H) 3.92-4.00 (m, 2H) 7.22-7.29 (m, 2H) 7.70-7.80 (m, 3H). LCMS (M+H)+=388.

Sources & evidence

ORD record
ord-6d871a23fd4b4d209b8518794975d142
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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