Tetrahydrofuran → 4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinoline

HRID 457721Notes

Reaction equation

[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1I)=[CH:9][CH:8]=[CH:7][CH:6]=2.O1CCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:24]1[C:32]2[C:27](=[CH:28][N:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1>CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O>[N:24]1([C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[CH:3][C:2]=2[F:1])[C:32]2[CH:31]=[CH:30][N:29]=[CH:28][C:27]=2[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Fluoro-4-iodo-quinoline (0.2 g, 0.73 mmol) was placed in a 25 ml round bottomed flask and to it was added tetrahydrofuran (15 ml), xantphos (0.015 g, 0.02 mmol), cesium carbonate (0.476 g, 1.4 mmol), 5-azaindoline (0.087 g, 0.73 mmol). The mixture was degassed for 5 mins. Tris(dibenzylidineacetone) dipalladium(0) (0.0025 g, 0.0025 mmol) was added and the mixture was heated to 80° C. for 48 hrs. Water was and compound extracted into ethyl acetate, dried over sodium sulfate and concentrated in rotary evaporator to yield desired compound (0.132 g, 67%). MS (ES) 266.1 (M+H)+

Workup

customThe mixture was degassed for 5 mins
extractioncompound extracted into ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated in rotary evaporator

Sources & evidence

ORD record: ord-a0e6120b3975429e9d56896aa044c28e
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189733B2

Reaction notes

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