Sodium Carbonate → 2-(5-Chloro-thiophen-2-yl)-4-(2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinoline

HRID 457723Notes

Reaction equation

[N:1]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12](I)[C:11]=2[F:21])[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:28][C:29]1[S:33][C:32](B(O)O)=[CH:31][CH:30]=1>O1CCCC1>[Cl:28][C:29]1[S:33][C:32]([C:12]2[C:11]([F:21])=[C:10]([N:1]3[C:9]4[CH:8]=[CH:7][N:6]=[CH:5][C:4]=4[CH2:3][CH2:2]3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-2-iodo-quinoline from step B (0.025 g, 0.063 mmol) was dissolved in tetrahydrofuran (5 ml) in a 25 ml round bottomed flask equipped with a magnetic stirrer. Sodium carbonate (0.06 g, 0.1 mmol) was added followed by 5-chlorothiophene-2-boronic acid (0.019 g, 0.08 mmol) and the mixture was degassed for 5 mins. Tetrakis(triphenylphosphine)-palladium(0) (5 mg, 5 mol %) was added followed by 0.5 ml water and the reaction mixture was heated to 80° C. for 4 hrs. The compound was extracted with ethyl acetate, dried and concentrated in vacuo. The title compound was purified by HPLC over a reverse phase column using a gradient of acetonitrile and water containing 0.1% trifluoroacetic acid to yield desired compound (0.012 g, 52%). MS (ES) 482.4 (M+H)+

Workup

customequipped with a magnetic stirrer
customthe mixture was degassed for 5 mins
additionTetrakis(triphenylphosphine)-palladium(0) (5 mg, 5 mol %) was added
extractionThe compound was extracted with ethyl acetate
customdried
concentrationconcentrated in vacuo
customThe title compound was purified by HPLC over a reverse phase column

Sources & evidence

ORD record: ord-b1105248c82242c5b6b3bd5424dce45a
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189733B2

Reaction notes

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