Sodium Carbonate → ethyl 3-phenyl-1H-indole-2-carboxylate

HRID 916189Notes

Reaction equation

HRID 916189 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1Br)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Product 1

HCID 2763656ethyl 3-phenyl-1H-indole-2-carboxylateYield 68.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-bromo-1H-indolecarboxylic acid ethyl ester (0.50 g, 1.87 mmol), phenylboronic acid (0.27 g, 2.25 mmol), 2 M aqueous sodium carbonate (8 mL), tetrakis(triphenylphosphine)palladium (0) (0.20 g, 0.17 mmol) in ethanol (16 mL) and toluene (30 ml) was heated at 65° C. for 16 h and then cooled. The reaction mixture was diluted with 1 N hydrochloric acid and then extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and concentrated. Flash silica gel chromatography using ethyl acetate/hexane as elutant gave 0.34 g (68%) of 3-phenyl-1H-indolecarboxylic acid ethyl ester as a pink solid: 1H NMR (DMSO-d4) δ 1.18 (t, J=7.2 Hz, 3H), 4.22 (q, J=7.2 Hz, 2H), 7.07-7.11 (m, 1H), 7.29-7.33 (m, 1H) 7.45 (dd, J=8.3, 0.8 Hz, 1H), 7.48-7.50 (m, 5H), 7.50 (dd, J=8.3, 0.8 Hz, 1H), 11.90 (br s, 1H); MS (ESI) m/z 266 (MH+); 264 ([M−H]−).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29385d24dce247578f1a4a540ea1c489
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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