Ethanesulfonamide → US10023592, Example 160

HRID 518378Notes

Reaction equation

HRID 518378 reaction equation
BrC1C2C(=CC(F)=CC=2)C(=O)NC=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.FC1C=C2C(C(B3OC(C)(C)C(C)(C)O3)=CN(C)C2=O)=CC=1.ClC1C(OCC2CC2)=CN=C(S(C)(=O)=O)N=1.[CH:70]1([CH2:73][O:74][C:75]2[C:76]([C:85]3[C:94]4[C:89](=[CH:90][C:91]([F:95])=[CH:92][CH:93]=4)[C:88](=[O:96])[N:87]([CH3:97])[CH:86]=3)=[N:77][C:78](S(C)(=O)=O)=[N:79][CH:80]=2)[CH2:72][CH2:71]1.[CH2:98]([S:100]([NH2:103])(=[O:102])=[O:101])[CH3:99]>>[CH:70]1([CH2:73][O:74][C:75]2[C:76]([C:85]3[C:94]4[C:89](=[CH:90][C:91]([F:95])=[CH:92][CH:93]=4)[C:88](=[O:96])[N:87]([CH3:97])[CH:86]=3)=[N:77][C:78]([NH:103][S:100]([CH2:98][CH3:99])(=[O:102])=[O:101])=[N:79][CH:80]=2)[CH2:71][CH2:72]1

Participants

7

Reactant 6

HCID 73702EthanesulfonamideHCID 2733548Bis(pinacolato)diboraneHCID 847030324-Bromo-7-fluoro-1,2-dihydroisoquinolin-1-oneHCID 1180218984-[5-(Cyclopropylmethoxy)-2-methylsulfonylpyrimidin-4-yl]-7-fluoro-2-methylisoquinolin-1-oneHCID 1180224454-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidineHCID 1238018347-Fluoro-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one

Product 1

HCID 118022460US10023592, Example 160

Procedure

The title compound of Example 58, step 2 was treated with 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane in a manner similar to Example 89, step 1 and the resulting 7-fluoro-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one was coupled to the title compound of Example 152, step 4 in a manner similar to Example 152, step 5 and the resulting 4-[5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidin-4-yl]-7-fluoro-2-methylisoquinolin-1-one was treated with with EtSO2NH2 instead of MeSO2NH2 in a manner similar to Example 152, step 6 to give the title compound. 1H NMR (CDCl3 400 MHz) δ 8.53 (dd, J1=8.8 Hz, J2=6.0 Hz, 1H), 8.40 (s, 1H), 7.77 (s, 1H), 7.69 (dd, J=8.8 Hz, 1H), 7.27-7.23 (m, 1H), 3.88 (d, J=6.8 Hz, 2H), 3.69 (s, 3H), 3.60 (q, J=7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H), 1.16-1.13 (m, 1H), 0.62-0.56 (m, 2H), 0.27-0.26 (m, 2H). LCMS: 433.2 (M+1)+

Sources & evidence

ORD record
ord-dd9bc356249349c2b6b444e1ce0b4d89
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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