Potassium Carbonate → 2-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

HRID 1404145Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13](=[O:19])[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([O:20][CH3:21])[CH:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.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>[CH2:11]([N:8]1[C:9]2[C:5](=[C:4]([O:20][CH3:21])[CH:3]=[C:2]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:10]=2)[C:6]([C:13](=[O:19])[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:7]1)[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To a sealable vessel was added 36-3 (100 mg, 0.28 mmol), phenylboronic acid (1042 mg, 0.86 mmol), Pd(PPh3)4 (66 mg, 10 mol %), and potassium carbonate (117 mg, 0.85 mmol). Dioxane (1.5 mL) was added and the reaction heated at 100° C. two days. The reaction mixture was diluted with ethyl acetate, filtered through celite and concentrated. The resulting residue was purified on silica gel column chromatography eluting with hexanes/ethylacetate (50-100%) to afford 79 mg of 36-4. LCMS: calc 350.2 and found: 351.1 [MH]+.

Workup

filtrationfiltered through celite and
concentrationconcentrated
customThe resulting residue was purified on silica gel column chromatography
washeluting with hexanes/ethylacetate (50-100%)

Sources & evidence

ORD record: ord-b54a8d37fb554dafa6ea47bbed9a2f28
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912220B2

Reaction notes

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