Ethyl Acetate → HCID 58896835, compound

HRID 522206Notes

Reaction equation

HRID 522206 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16](B(O)O)[CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>O1CCCC1.O.C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-2](Cl)CC=CC1C=CC=CC=1)(C)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[C:14]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][CH:9]=[CH:10][C:3]=23)[CH:13]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 58896835HCID 58896835, compound

Reagents, catalysts & solvents 3

HCID 178439028HCID 178439028, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine (15 g, 98 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (18.38 g, 108 mmol), potassium phosphate (62.6 g, 295 mmol), and {1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene}chloro {3-phenylallyl}palladium(II) (0.637 g, 0.983 mmol) in tetrahydrofuran (400 mL) and water (133 mL) was purged with nitrogen and heated at 65° C. overnight. The mixture was cooled and poured into water. Ethyl acetate was added, the mixture was stirred for 15 minutes and the organic layer was washed with brine. The combined aqueous extracts were extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was dissolved in dichloromethane and placed on a bed of silica gel equilibrated in 30% ethyl acetate/heptanes that was packed in a coarse Buchner funnel. The material was eluted with 30-40% ethyl acetate/heptanes to provide the title compound. MS (ESI+) m/z 243.2 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. washthe organic layer was washed with brine
  3. extractionThe combined aqueous extracts were extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. washThe material was eluted with 30-40% ethyl acetate/heptanes

Sources & evidence

ORD record
ord-9e83d9dd8ffc4f4a9cb04ed36e15563d
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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