Sodium Carbonate → HCID 68324044, compound

HRID 573660Notes

Reaction equation

Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:37][N:38]1[CH:42]=[C:41](B(O)O)[CH:40]=[N:39]1>C(#N)C.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:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:41]4[CH:40]=[N:39][N:38]([CH3:37])[CH:42]=4)=[C:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (Example 33) (50 mg, 0.095 mmol), tetrakis(triphenylphosphine)palladium(0) (5.51 mg, 4.77 μmol), sodium carbonate (20.23 mg, 0.191 mmol) and (1-methyl-1H-pyrazol-4-yl)boronic acid (12.02 mg, 0.095 mmol) in acetonitrile (1 mL) and water (0.250 mL) was heated at 80° C. under nitrogen, overnight (ca. 18 h). The reaction mixture was then cooled to RT and concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-50% ethyl acetate in DCM, to give the title compound (17.5 mg). LCMS (A) m/z: 525 [M+1]+, Rt 1.34 min (acidic).

Workup

temperatureThe reaction mixture was then cooled to RT
concentrationconcentrated
customThe residue was purified by chromatography on silica
washeluting with a gradient of 0-50% ethyl acetate in DCM

Sources & evidence

ORD record: ord-b115f643007e4c5994e1696822c2a1a1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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