Potassium Phosphate, Tribasic → HCID 89741045, compound

HRID 2206475Notes

Reaction equation

HRID 2206475 reaction equation
[C:1]1([CH3:22])[C:2]([NH:7][CH:8]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2Br)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][CH:4]=[CH:5][CH:6]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O>[C:1]1([CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8]1

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 131733192HCID 131733192, compound

Product 1

HCID 89741045HCID 89741045, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
77.5 °C

Procedure

A mixture of ethyl 3-(o-toluidino)-2-(2-bromophenyl)acrylate (1.326 g, 3.68 mmol), cuprous iodide (38 mg, 0.38 mmol), potassium phosphate (1.652 g, 7.8 mmol) and N,N-dimethylformamide (16 mL) was stirred at 75-80° C. under nitrogen gas atmosphere for 16 hours. The reaction mixture was allowed to cool to room temperature. Solvent was removed under reduced pressure. Water (16 mL) was added to the residue and the mixture was extracted with ethyl acetate (8 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1) to give pure ethyl 1-(o-tolyl)-1H-indole-3-carboxylate as a pale yellow solid (0.789 g, 77%). LRMS (M+H+) m/z: calcd 279.13. found 279. 1H NMR (300 MHz, CDCl3): δ 8.26 (dd, J=7.9, 0.7 Hz, 1H), 7.89 (d, J=0.7 Hz, 1H), 7.53-7.11 (m, 6H), 7.02 (dd, J=8.1, 0.8 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 2.07 (s, 3H), 1.45 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureto cool to room temperature
  2. customSolvent was removed under reduced pressure
  3. additionWater (16 mL) was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate (8 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a residue
  10. customThe residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-54b911f749214b048f332f6f1517c0a6
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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