2-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzene → US10023592, Example 377

HRID 518538Notes

Reaction equation

HRID 518538 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2B2OC(C)(C)C(C)(C)O2)[CH2:3][CH2:2]1.BrC1C=C(S(C)(=O)=[O:33])C=CC=1OCC1CC1.Br[C:42]1[C:51]2[C:46](=[CH:47][CH:48]=C(C(F)(F)F)C=2)[C:45](=[O:56])[N:44]([CH3:57])[CH:43]=1>>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:13])=[O:14])=[CH:8][C:7]=2[C:42]2[C:51]3[O:33][CH:48]=[CH:47][C:46]=3[C:45](=[O:56])[N:44]([CH3:57])[CH:43]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 1180216932-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzeneHCID 1180220564-Bromo-2-methyl-6-(trifluoromethyl)isoquinolin-1-oneHCID 1234348592-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118022339US10023592, Example 377

Procedure

The title compound was prepared in a manner similar to Example 197, by substituting 5-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[3,2-c]pyridin-4-one for 2-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 2-bromo-1-(cyclopropylmethoxy)-4-methylsulfonylbenzene for 4-bromo-2-methyl-6-(trifluoromethyl)isoquinolin-1-one. 1H NMR (CDCl3, 400 MHz) δ 8.05 (s, 1H), 7.92 (dd, J1=8.6 Hz, J2=1.8 Hz, 1H), 7.50 (m, 2H), 7.07 (m, 2H), 3.95 (d, J=6.7 Hz, 2H), 3.70 (s, 3H), 3.1 (s, 3H), 1.15 (m, 1H), 0.57 (m, 2H), 0.28 (m, 2H). LCMS: 374.1 (M+H)+

Sources & evidence

ORD record
ord-d0f9e43d40004cdfa5694161562697c3
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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