Potassium Carbonate → HCID 68323747, compound

HRID 573646Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:22])=[CH:8][C:9]=2[NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)(=[O:14])=[O:13])[S:4][C:3]=1[CH3:23].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30](B(O)O)[CH:31]=2)[CH:26]=[CH:25]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:21][C:17]1[CH:16]=[C:15]([S:12]([NH:11][C:9]2[CH:8]=[C:7]([CH3:22])[N:6]=[C:5]3[S:4][C:3]([CH3:23])=[C:2]([C:30]4[CH:31]=[C:32]5[C:27]([CH:26]=[CH:25][NH:24]5)=[CH:28][CH:29]=4)[C:10]=23)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Under nitrogen, N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 61) (16.6 mg, 0.038 mmol) was dissolved in 1,4-dioxane (0.6 mL) and water (0.2 mL). 1H-Indol-6-ylboronic acid (9.28 mg, 0.058 mmol), tetrakis(triphenylphosphine)palladium(0) (4.44 mg, 3.84 μmol) and potassium carbonate (10.63 mg, 0.077 mmol) were then added and the mixture heated in a microwave at 120° C. for 15 min. The crude mixture was purified by MDAP (acidic conditions) and then further purified by normal phase chromatography, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, to give the title compound (3 mg). LCMS (A) m/z: 468 [M+1]+, Rt 1.45 min (acidic).

Workup

customThe crude mixture was purified by MDAP (acidic conditions)
customfurther purified by normal phase chromatography
washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-cff771c9a81a424b9173559bf521fe8e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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