Potassium Hydroxide → HCID 89876014, compound

HRID 1487070Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([S:10]([N:13]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[CH3:25])[CH2:14][CH:15]([CH3:17])[CH3:16])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH:8]=[CH2:9].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[OH-].[K+].[O:58]1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:25][C:19]1[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=1[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[S:10]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH2:9])=[C:2]([OH:58])[CH:3]=1)(=[O:12])=[O:11]

Participants

Conditions

Temperature: 150 °C

Procedure

3-chloro-N-(2,4-dimethylphenyl)-N-isobutyl-4-vinylbenzenesulfonamide (250 mg, 0.662 mmol), tris(dibenzylideneacetone)dipalladium(0) (6.06 mg, 6.62 μmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (2.81 mg, 6.62 μmol) and potassium hydroxide (111 mg, 1.985 mmol) were added to a microwave vial. 1,4-dioxane (1 mL) and water (1.000 mL) were then added. The reaction vessel was sealed and heated by microwaves (Biotage Initiator) to 150° C. for 2 hours. LCMS analysis showed the desired product and several side-products. The crude material was purified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the required product, 100.8 mg, as a yellow gum. LCMS [LCMS2] Rt 1.42 min, m/z (ES+) 360 (M+H).

Workup

customThe reaction vessel was sealed

Sources & evidence

ORD record: ord-030b1759c1064026931b104f69c08f4a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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