1-(2-Cyclopropylethyl)-2-iodo-4-methylsulfonylbenzene → US10023592, Example 319

HRID 518513Notes

Reaction equation

HRID 518513 reaction equation
[CH:1]1([CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2I)[CH2:3][CH2:2]1.[CH3:17][N:18]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:37]>>[CH:1]1([CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:26]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:37])[N:18]([CH3:17])[CH:27]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 1180219661-(2-Cyclopropylethyl)-2-iodo-4-methylsulfonylbenzeneHCID 1238094992-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one

Product 1

HCID 118021518US10023592, Example 319

Procedure

The title compound of Example 315, step 3 was reacted with the title compound of Example 89, step 1 in a manner similar to Example 315, step 4 to give the title compound. 1H NMR (CD3OD, 400 MHz): δ 8.67 (d, J=8.0 Hz, 1H), 8.21 (dd, J1=2.0 Hz, J2=6.0 Hz, 1H), 8.03 (d, J=2.0 Hz, 1H), 7.92-7.86 (m, 2H), 7.82-7.79 (m, 1H), 7.61 (s, 1H), 7.28 (d, J=8.0 Hz, 1H), 3.91 (s, 3H), 3.38 (s, 3H), 2.94-2.89 (m, 1H), 2.83-2.77 (m, 1H), 1.64-1.55 (m, 2H), 0.75-0.71 (m, 1H), 0.51-0.47 (m, 2H), 0.01-0.00 (m, 2H). LCMS: 382 (M+1)+

Sources & evidence

ORD record
ord-e482c1d0000b457294ca33af9eecbe0f
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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