3-Bromo-4-methylpyridine → N-(4-(4-Methylpyridin-3-yl)-3-(trifluoromethyl)phenyl)methanesulfonamide
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1C1C=CC=C2C=1C=NN2.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][C:26]=2[C:36]([F:39])([F:38])[F:37])O1.BrC1C=NC=CC=1C>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:25]1[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])=[CH:27][C:26]=1[C:36]([F:37])([F:38])[F:39]Participants
Reactant 3
Product 1
Procedure
The compound of Example 240 was prepared by the procedure described for the preparation of Intermediate 1C using Intermediate 52 and 3-bromo-4-methylpyridine. The crude material was purified by reverse phase preparative HPLC using a PHENOMENEX® Luna 30×100 mm column with a linear gradient of Solvent A (10% methanol/90% water with 0.1% TFA) and Solvent B (90% methanol/10% water with 0.1% TFA) over 12 min with peak detection at 254 nM. Collected fractions were applied to a 1 g Waters OASIS® MCX cation exchange cartridge, which was washed with methanol and 2 M ammonia in methanol, to provide the title compound (43 mg, 58%) as a solid: HPLC Ret timed: 1.21 min. MS: m/z=331 [M+H]+; 1H NMR (400 MHz, CD3OD) δ ppm 8.42 (1 H, d, J=5.0 Hz), 8.24 (1 H, s), 7.70 (1 H, s), 7.60 (1 H, d, J=8.3 Hz), 7.24-7.49 (2 H, m), 3.09 (3 H, s), 2.12 (3 H, s); 19F NMR (CD3OD) δ ppm 60.8.
Workup
- customThe crude material was purified by reverse phase preparative HPLC
- customover 12 min
- washwas washed with methanol and 2 M ammonia in methanol
Sources & evidence
- ORD record
- ord-25321d04e2284515ade8a5898b94839d
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916553B2
Reaction notes
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