Dimethylformamide → Irsenontrine

HRID 1043971Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([C@H:16]4[CH2:20][CH2:19][O:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[CH3:21][O:22][C:23]1[C:28]([CH3:29])=[C:27](B(O)O)[C:26]([CH3:33])=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>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.O>[CH3:21][O:22][C:23]1[C:28]([CH3:29])=[C:27]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:15]([C@H:16]5[CH2:20][CH2:19][O:18][CH2:17]5)[N:14]=[CH:13][C:7]=4[C:8](=[O:12])[NH:9][C:10]=3[CH:11]=2)[C:26]([CH3:33])=[CH:25][N:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(S)-7-bromo-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one (100 mg), (2-methoxy-3,5-dimethyl-pyridin-4-yl)boronic acid (65 mg) obtained in Preparation Example 29 (4) and cesium carbonate (293 mg) were added to a mixed solution of DMF (5 mL) and water (1 mL) at room temperature. PdCl2(PPh3)2 (10.5 mg) was added to the mixture in a nitrogen gas stream. The mixture was stirred at 80° C. for one hour and at 100° C. for 4.5 hours. After cooling the reaction mixture to room temperature, water (5 mL) was added, and the mixture was extracted with isopropyl acetate. The organic layer was washed with water and brine and then concentrated under reduced pressure. A crude purified product (64.7 mg) was obtained as the title compound. The instrumental data of this compound were identical to those of the (−)-form of Example 25.

Workup

temperatureAfter cooling the reaction mixture to room temperature
extractionthe mixture was extracted with isopropyl acetate
washThe organic layer was washed with water and brine
concentrationconcentrated under reduced pressure
customA crude purified product (64.7 mg)

Sources & evidence

ORD record: ord-261d236098c04660b56b4640e6b2f56c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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