Ethanesulfonamide → US10023592, Example 157

HRID 518375Notes

Reaction equation

HRID 518375 reaction equation
BrC1C2C(=CC=C(F)C=2)C(=O)N(C)C=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.FC1C=C2C(=CC=1)C(=O)N(C)C=C2B1OC(C)(C)C(C)(C)O1.ClC1C(OCC2CC2)=CN=C(S(C)(=O)=O)N=1.[CH:71]1([CH2:74][O:75][C:76]2[C:77]([C:86]3[C:95]4[C:90](=[CH:91][CH:92]=[C:93]([F:96])[CH:94]=4)[C:89](=[O:97])[N:88]([CH3:98])[CH:87]=3)=[N:78][C:79](S(C)(=O)=O)=[N:80][CH:81]=2)[CH2:73][CH2:72]1.[CH2:99]([S:101]([NH2:104])(=[O:103])=[O:102])[CH3:100]>>[CH:71]1([CH2:74][O:75][C:76]2[C:77]([C:86]3[C:95]4[C:90](=[CH:91][CH:92]=[C:93]([F:96])[CH:94]=4)[C:89](=[O:97])[N:88]([CH3:98])[CH:87]=3)=[N:78][C:79]([NH:104][S:101]([CH2:99][CH3:100])(=[O:103])=[O:102])=[N:80][CH:81]=2)[CH2:72][CH2:73]1

Participants

7

Reactant 6

HCID 73702EthanesulfonamideHCID 2733548Bis(pinacolato)diboraneHCID 1180215214-Bromo-6-fluoro-2-methylisoquinolin-1-oneHCID 1180224454-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidineHCID 1180226014-[5-(Cyclopropylmethoxy)-2-methylsulfonylpyrimidin-4-yl]-6-fluoro-2-methylisoquinolin-1-oneHCID 1317328506-Fluoro-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one

Product 1

HCID 118022276US10023592, Example 157

Procedure

The title compound of Example 47, 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 6-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]-6-fluoro-2-methylisoquinolin-1-one was treated with EtSO2NH2 instead of MeSO2NH2 in a manner similar to Example 152, step 6 to give the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 11.04 (brs, 1H), 8.54 (s, 1H), 8.36 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 8.01 (s, 1H), 7.65 (dd, J1=11.2 Hz, J2=2.4 Hz, 1H), 7.45-7.38 (m, 1H), 3.95 (d, J=6.8 Hz, 2H), 3.58 (s, 3H), 3.48 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H), 1.16-1.04 (m, 1H), 0.50-0.42 (m, 2H), 0.27-0.20 (m, 2H). LCMS: 433.0 (M+1)+

Sources & evidence

ORD record
ord-ff52b4b24a03491aaa3806854322b7fb
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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