Cesium carbonate → HCID 71080417, compound

HRID 921011Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)[CH:17]=[CH:16]2

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-2-(trifluoromethyl)pyridine (2.075 g, 9.18 mmol) was added to a solution of 5-bromo-1H-indole (1.5 g, 7.65 mmol) and in DMF (20 mL) followed by cesium carbonate (7.48 g, 22.95 mmol), and the mixture was stirred at 90° C. for 15 min. Insoluble solids were filtered, filtrate was concentrated and partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography using 5% ethyl acetate in pet ether to afford title compound (1.1 g, 42.1%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 9.09 (d, J=2.4 Hz, 1H), 8.37 (dd, J1=2.4 Hz, J2=8.4 Hz, 1H), 8.11 (d, J=8.4 Hz, 1H), 7.91 (m, 2H), 7.68 (d, J=9.0 Hz, 1H), 7.37 (dd, J1=1.8 Hz, J2=8.4 Hz, 1H), 6.82 (d, J=3.0 Hz, 1H).

Workup

filtrationInsoluble solids were filtered
concentrationfiltrate was concentrated
custompartitioned between ethyl acetate and water
customOrganic layer was separated
washwashed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
custompurified by flash chromatography

Sources & evidence

ORD record: ord-8d94998b412749838b2b8709af708f76
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273069B2

Reaction notes

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