Sodium Carbonate → HCID 9863458, compound

HRID 382062Notes

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5](B(O)O)[C:4]=2[CH:3]=[CH:2]1.Br[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1/[C:16](=[CH:24]/[C:25]1[NH:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31])/[C:17](=[O:23])[NH:18]2.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[NH:1]1[C:9]2[C:4](=[C:5]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3/[C:16](=[CH:24]/[C:25]3[NH:26][CH:27]=[CH:28][C:29]=3[O:30][CH3:31])/[C:17](=[O:23])[NH:18]4)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 4-indoleboronic acid (64 mg, 0.40 mmol) (from Step A above), (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (100 mg, 0.31 mmol) (Starting Material 7), and sodium carbonate (35 mg, 0.33 mmol) in 3 mL DME and 1 mL water was degassed for 15 min. by bubbling argon through the solution. Dichlorobis(triphenylphosphine)palladium (II) (13 mg) (Aldrich) was then added and the reaction was heated at 90° C. for 2 days. The reaction was then poured into 100 mL water and the product was extracted with ethyl acetate (4×50 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The product was purified via flash column chromatography (1% CH3OH in CHCl3) to yield 42 mg (38%) orange powder.

Workup

customby bubbling argon through the solution
additionDichlorobis(triphenylphosphine)palladium (II) (13 mg) (Aldrich) was then added
additionThe reaction was then poured into 100 mL water
extractionthe product was extracted with ethyl acetate (4×50 mL)
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe product was purified via flash column chromatography (1% CH3OH in CHCl3)

Sources & evidence

ORD record: ord-2c33267ad27f4cf6b1fd3784150e18ce
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06307056B1

Reaction notes

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