Cesium carbonate → HCID 71080376, compound

HRID 921006Notes

Reaction equation

HRID 921006 reaction equation
[F:1][CH:2]([F:5])[CH2:3]I.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[N:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:6][C:7]1[CH:8]=[C:9]2[CH:10]=[CH:11][N:12]([CH2:3][CH:2]([F:5])[F:1])[C:13]2=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 38335651,1-Difluoro-2-iodoethaneHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 71080376HCID 71080376, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1,1-Difluoro-2-iodoethane (2.19 g, 11.42 mmol) was added to a solution of 5-bromo,7-azaindole (1.5 g, 7.61 mmol) in DMF (30 mL) followed by cesium carbonate (4.96 g, 15.2 mmol), and the mixture was stirred at 70° C. for 1 h. Insoluble solids were filtered off, and filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in reduced pressure and purified by flash chromatography using 5% ethyl acetate in hexane to afford title compound (1.3 g, 65%) as oil. 1H NMR (300 MHz, CDCl3): δ 8.33 (d, J=2.1 Hz, 1H), 8.04 (d, J=2.4 Hz, 1H), 7.26 (d, J=2.1 Hz, 1H), 6.46 (d, J=3.6 Hz, 1H), 6.28-5.88 (tt, J1=3.9 Hz, J2=55.8 Hz, 1H), 4.60 (dt, J1=4.2 Hz, J2=14.1 Hz, 2H).

Workup

  1. filtrationInsoluble solids were filtered off
  2. concentrationfiltrate was concentrated
  3. customResidue was partitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in reduced pressure
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ecf97052cfd14d149cdb666dcf8f2956
Source dataset
uspto-grants-2016_03
Patent number
US09273069B2

Reaction notes

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