Ethanesulfonyl chloride → US10023592, Example 218

HRID 518419Notes

Reaction equation

HRID 518419 reaction equation
C1(CO)CC1.C[O-].[Na+].CS(Cl)(=O)=O.C(S(Cl)(=O)=O)C.[CH3:20][N:21]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[C:22]1=[O:40].[Br:41][C:42]1[C:43]([O:54][CH2:55][CH:56]2[CH2:58][CH2:57]2)=[CH:44][C:45]([F:53])=[C:46]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])[CH:47]=1>>[Br:41][C:42]1[C:43]([O:54][CH2:55][CH:56]2[CH2:58][CH2:57]2)=[CH:44][C:45]([F:53])=[C:46]([NH:48][S:49]([CH3:52])(=[O:50])=[O:51])[CH:47]=1.[CH:56]1([CH2:55][O:54][C:43]2[C:42]([C:29]3[C:28]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[C:22](=[O:40])[N:21]([CH3:20])[CH:30]=3)=[CH:47][C:46]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])=[C:45]([F:53])[CH:44]=2)[CH2:57][CH2:58]1

Participants

8

Reactant 6

HCID 11667Ethanesulfonyl chlorideHCID 31297Methanesulfonyl chlorideHCID 75644CyclopropanemethanolHCID 10942334Sodium MethoxideHCID 118022043N-[5-bromo-4-(cyclopropylmethoxy)-2-fluorophenyl]methanesulfonamideHCID 1238019002-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroisoquinolin-1-one

Product 2

HCID 118022040US10023592, Example 218HCID 118022043N-[5-bromo-4-(cyclopropylmethoxy)-2-fluorophenyl]methanesulfonamide

Procedure

N-[5-bromo-4-(cyclopropylmethoxy)-2-fluorophenyl]methanesulfonamide was prepared in 3 steps in a similar manner as Example 86 except that the alkoxide of cyclopropylmethanol was substituted for sodium methoxide in step 1 and methanesulfonylchloride was substituted for ethansulfonylchloride in step 3. The title compound of Example 163, step 3 and N-[5-bromo-4-(cyclopropylmethoxy)-2-fluorophenyl]methanesulfonamide were reacted in a similar manner as in Example 89, step 2 to give the title compound. 1H NMR (CDCl3, 400 MHz): δ 7.29 (d, J=9.2 Hz, 1H), 6.96 (s, 1H), 6.70 (d, J=12.0 Hz, 1H), 6.21 (s, 1H), 3.76-3.75 (m, 2H), 3.56 (s, 3H), 3.02 (s, 3H), 2.70-2.60 (m, 2H), 2.36-2.17 (m, 2H), 1.80-1.70 (m, 2H), 1.69-1.64 (m, 2H), 1.20-1.10 (m, 1H), 0.60-0.50 (m, 2H), 0.27-0.25 (m, 2H). LCMS: 421.1 (M+H)+

Sources & evidence

ORD record
ord-f1a33266247c46b1a79d5663b27d26ad
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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