Phenylboronic Acid → HCID 57948698, compound

HRID 555341Notes

Reaction equation

C([N:8]1[C:16]2[C:11](=[CH:12][C:13](Cl)=[CH:14][CH:15]=2)[C:10]2([C:23]3[NH:24][C:25]4[C:30]([C:22]=3[CH2:21][CH2:20][CH2:19][NH:18]2)=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:9]1=[O:31])C1C=CC=CC=1.[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[C:41](=O)(O)[O-].[Na+]>CN(C=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>[CH3:41][CH:19]1[NH:18][C:10]2([C:11]3[C:16](=[CH:15][CH:14]=[C:13]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:12]=3)[NH:8][C:9]2=[O:31])[C:23]2[NH:24][C:25]3[C:30]([C:22]=2[CH2:21][CH2:20]1)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of compound 1 (7 mg, 0.018 mmol), benzeneboronic acid (2.6 mg, 0.021 mmol) and tetrakis(triphenylphosphine)palladium (2 mg, 0.002 mmol) in DMF (2 mL)/aqueous 2 N sodium bicarbonate solution (0.5 mL) is stirred for 20 minutes in a microwave reactor at 130° C. After being cooled to room temperature, the reaction mixture is extracted with ethyl acetate (3×10 mL). The combined organic phases are dried over sodium sulfate and concentrated in vacuo. The residue is subjected to flash column chromatography (silica gel, 30% EtOAc in hexanes) to afford compound 29 (2.3 mg, 33%) as white solid.

Workup

temperatureAfter being cooled to room temperature
extractionthe reaction mixture is extracted with ethyl acetate (3×10 mL)
dry with materialThe combined organic phases are dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-410b88afe1364f3c97053ec2317d86c7
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053442B2

Reaction notes

Loading…