Sulfuric Acid → 3-(3-Trifluoromethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid

HRID 1888541Notes

Reaction equation

Br[C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.S(=O)(=O)(O)O>C(#N)C.C(=O)([O-])[O-].[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[C:24]([C:2]2[CH:17]=[N:16][C:5]3[NH:6][C:7]4[CH:12]=[N:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=4[C:4]=3[CH:3]=2)[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A degassed mixture of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid (20.0 mg, 68.5 μmol), 3-(trifluoromethyl)phenylboronic acid (19.5 mg, 0.103 mmol), and bis(triphenylphosphine)palladium(II) dichloride (2.4 mg, 3.4 μmol) in acetonitrile (0.3 mL) and 2N aqueous sodium carbonate solution (0.3 mL) was heated under microwave irradiation at 140° C. for 10 minutes. The cooled reaction mixture was acidified with 10% aqueous sulfuric acid. The solid was removed by filtration and the resultant filtrate was purified by preparative HPLC (5-45% MeCN over 45 min, 35 mL/min) to afford the title compound. 1H NMR (DMSO-D6, 400 MHz): 12.75 (s, 1H), 9.38-9.00 (m, 3H), 8.21 (m, 1H), 7.78 (m, 2H), 7.65-7.60 (m, 2H). LCMS (Method D): RT=10.76 min, M+H+=358.

Workup

customThe cooled reaction mixture
customThe solid was removed by filtration
customthe resultant filtrate was purified by preparative HPLC (5-45% MeCN over 45 min, 35 mL/min)

Sources & evidence

ORD record: ord-b127f45286e845eba5d080f72ffb9520
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501765B2

Reaction notes

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