Hydrochloric Acid → HCID 59774845, compound

HRID 2387273Notes

Reaction equation

HRID 2387273 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([OH:10])[CH:9]=[C:4]2[CH:3]=[CH:2]1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>N1C=CC=CC=1.[Cu-]=O>[O:10]([C:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][NH:1][C:5]2=[N:6][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-ol

Product 1

HCID 59774845HCID 59774845, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

To 1H-Pyrrolo[2,3-b]pyridin-5-ol (6, 645 mg, 4.81 mol) and copper(I) oxide (860 mg, 6.0 mmol) in pyridine (10 mL), bromobenzene (31, 422 uL, 4.01 mmol) was added. The mixture was heated to 115° C. for 24 hours. The reaction mixture was treated with 1N HCl and extracted with ethyl acetate. The organic layer was washed with NH4OH/NH4Cl (1:4), saturated aqueous NH4Cl twice, water, and brine, dried over anhydrous magnesium sulfate, filtrated and concentrated. The desired compound was isolated with silica gel column chromatography (50-70% ethyl acetate/hexane) to provide the compound (P-0035, 88 mg, 10%). MS (ESI) [M+H+]+=211.2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with NH4OH/NH4Cl (1:4), saturated aqueous NH4Cl twice
  3. dry with materialwater, and brine, dried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dc78e94612b84287847576dd5c77421e
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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