Potassium Carbonate → HCID 68472197, compound

HRID 2382680Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH:8]2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]([S:17]([N:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH3:21])(=[O:19])=[O:18])=[C:4]([F:30])[CH:3]=1.BrC1[C:33]([Cl:39])=[CH:34][C:35]([CH3:38])=[N:36][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[CH:37]=[N:36][C:35]([CH3:38])=[CH:34][C:33]=2[Cl:39])=[CH:6][C:5]([S:17]([N:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH3:21])(=[O:19])=[O:18])=[C:4]([F:30])[CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

4-Chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-5-(4,4,5,5-tetramethyl-[1,3]dioxolan-2-yl)-benzenesulfonamide (57 mg, 0.125 mmol), 5-bromo-4-chloro-2-methyl-pyridine (21 mg, 0.1 mmol), Pd(Ph3P)4 (12 mg, 0.01 mmol), K2CO3 (69 mg, 0.5 mmol) in a mixture of dioxane (1.5 mL) and water (0.15 mL) was degassed with N2 for 5 min. The reaction vessel was sealed and heated at 85° C. for 14 hrs. After the filtration, the mixture was purified by prep. LCMS to afford 4-chloro-5-(4-chloro-6-methyl-pyridin-3-yl)-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzenesulfonamide 3-1. MS: 454.7 (M+H)+; tR=7.77 min (method 2). NMR (CDCl3), δ, 8.350 (1H, s), 7.549 (1H, d, J=6.9 Hz), 7.257-7.436 (5H, m), 6.932 (1H, m), 6.817 (1H, m), 3.513 (3H, s), 3.389 (3H, d, J=2.1 Hz), 2.656 (3H, s).

Workup

customwas degassed with N2 for 5 min
customThe reaction vessel was sealed
filtrationAfter the filtration
customthe mixture was purified by prep

Sources & evidence

ORD record: ord-b322e53a456445cbb29ab5d312d25bfa
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263588B2

Reaction notes

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