Potassium Carbonate → HCID 71080370, compound

HRID 535692Notes

Reaction equation

HRID 535692 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15]2[CH:21]=[CH:20][NH:19][C:16]2=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C=O)C.[Cu]Br.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:12][C:13]1[CH:14]=[C:15]2[CH:21]=[CH:20][N:19]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=3)[C:16]2=[N:17][CH:18]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 71080370HCID 71080370, compoundYield 23.1%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 24593copper(I) bromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Iodo-4-(trifluoromethyl)benzene (1.657 g, 6.09 mmol) was added to a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (1 g, 5.08 mmol) and Copper(I) bromide (0.073 g, 0.508 mmol) in DMF (10 mL) followed by potassium carbonate (1.75 g, 12.69 mmol), and the mixture was stirred at 100° C. for 10 min. NaOH (150 mg, 3.75 mmol) and copper(II) acetate (4.61 mg, 0.025 mmol) were added to the reaction mixture at 110° C., and the mixture was stirred for 16 h. Insoluble solids were filtered off, and the filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 10% ethyl acetate in pet ether to afford title compound (0.4 g, 22%) as a off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.4 (d, J=2.0 Hz, 1H), 8.11 (d, J=2.4 Hz, 1H), 7.93 (d, J=8.0 Hz, 2H), 7.78 (d, J=8.8 Hz, 2H), 7.56 (d, J=4.0 Hz, 1H), 6.63 (d, J=3.6 Hz, 1H).

Workup

  1. stirringthe mixture was stirred for 16 h
  2. filtrationInsoluble solids were filtered off
  3. concentrationthe filtrate was concentrated
  4. customResidue was partitioned between ethyl acetate and water
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-16ab87b1433a49589ec94160691a240a
Source dataset
uspto-grants-2014_10
Patent number
US08859536B2

Reaction notes

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