Phenylacetic Acid → HCID 69375012, compound

HRID 1019279Notes

Reaction equation

HRID 1019279 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH:20]=O)=[CH:12]1.C(OC(=O)C)(=O)C.CCN(CC)CC>>[NH:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH:20]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([OH:10])=[O:9])=[CH:12]1

Participants

5

Reactant 4

HCID 999Phenylacetic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 69375012HCID 69375012, compoundYield 44.3%

Conditions

Temperature
100 °C

Procedure

A mixture of phenylacetic acid (0.0376 mol., 5.1 g) and 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (0.0376 mol., 5.5 g) in acetic anhydride (0.1881 mol., 17.7 ml) and Et3N (0.0376 mol., 5.2 ml) was stirred at 100° C., for 6 hrs. The obtained solution was cooled to 50° C., quenched with conc. hydrochloric acid (10 ml) and extracted with EtOAc. The organic phase was extracted with 1 N NaOH. 3-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-2-phenyl-2-propenoic acid was then precipitated from the aqueous layer with conc. hydrochloric acid with ice-cooling. Filtration and recrystallization from isopropyl alcohol of the crude product afforded 4,4 g of the desired compound as a white solid (44%), m.p. >230° C.

Workup

  1. temperatureThe obtained solution was cooled to 50° C.
  2. customquenched with conc. hydrochloric acid (10 ml)
  3. extractionextracted with EtOAc
  4. extractionThe organic phase was extracted with 1 N NaOH
  5. custom3-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-2-phenyl-2-propenoic acid was then precipitated from the aqueous layer with conc. hydrochloric acid with ice-
  6. temperaturecooling
  7. filtrationFiltration and recrystallization from isopropyl alcohol of the crude product

Sources & evidence

ORD record
ord-3377006d5a6d416cac1c28ddd37f6c4e
Source dataset
uspto-grants-2002_11
Patent number
US06486322B1

Reaction notes

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