2-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzene → US10023592, Example 217

HRID 575688Notes

Reaction equation

HRID 575688 reaction equation
[CH3:1][N:2]1[CH:11]=[C:10](B2OC(C)(C)C(C)(C)O2)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]1=[O:21].Br[C:23]1[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:26]=[CH:25][C:24]=1[O:33][CH2:34][CH:35]1[CH2:37][CH2:36]1>>[CH:35]1([CH2:34][O:33][C:24]2[CH:23]=[CH:28][C:27]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:26][C:25]=2[C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[C:3](=[O:21])[N:2]([CH3:1])[CH:11]=2)[CH2:36][CH2:37]1

Participants

3

Reactant 2

HCID 1180216932-Bromo-1-(cyclopropylmethoxy)-4-(methylsulfonyl)benzeneHCID 1238019002-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroisoquinolin-1-one

Product 1

HCID 118021929US10023592, Example 217

Procedure

The title compound of Example 163, step 3 and 2-bromo-1-(cyclopropylmethoxy)-4-methylsulfonylbenzene were reacted in a similar manner as in Example 89, step 2 to give the title compound. 1H NMR (CDCl3, 400 MHz): δ 7.92 (dd, J1=8.4 Hz, J2=2.0 Hz, 1H), 7.70 (d, J=2.0 Hz, 1H), 7.06 (s, 1H), 7.02 (d, J=8.4 Hz, 1H), 3.92-3.87 (m, 2H), 3.62 (s, 3H), 3.08 (s, 3H), 2.70-2.60 (m, 2H), 2.40-2.30 (m, 2H), 1.77-1.64 (m, 4H), 1.21-1.17 (m, 1H), 0.63-0.61 (m, 2H), 0.29-0.27 (m, 2H). LCMS: 388.1 (M+H)+

Sources & evidence

ORD record
ord-f1c4188a23c14693a49d5f2996b7d643
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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