Hydrochloric Acid → 9-Benzenesulfonyl-5-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1505854Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23](Br)[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1.Cl>C([O-])(=O)C.[K+].C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23]([C:31]4[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=4)[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (500 mg, 1.16 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.40 mmol) and [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) (200 mg, 0.25 mmol) in 2N aqueous potassium acetate (3.6 mL) and acetonitrile (7.2 mL) was heated under microwave irradiation at 140° C., for 30 minutes. The reaction mixture was allowed to cool to ambient temperature, 1M hydrochloric acid (7.5 mL) was added and the mixture was stirred at room temperature for 1 h. The resulting precipitate was collected by filtration, washed with acetonitrile (5 mL) and left to air dry to afford the title compound as a crude brown solid (500 mg, 99%). LCMS (Method G): RT=3.84 min, M+H+=431.

Workup

temperatureto cool to ambient temperature
filtrationThe resulting precipitate was collected by filtration
washwashed with acetonitrile (5 mL)
waitleft to air
customdry

Sources & evidence

ORD record: ord-29140b9d7a5e489b9e5d3d4fd8e46c4e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216980B2

Reaction notes

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