methyl 1H-indole-5-carboxylate → HCID 57263143, compound

HRID 634269Notes

Reaction equation

HRID 634269 reaction equation
C[O-].[Na+].[C:4]([NH:7][OH:8])([NH2:6])=[NH:5].[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18](OC)=O)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1>>[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[O:8][N:7]=[C:4]([NH2:6])[N:5]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

4

Reactant 3

HCID 2737635methyl 1H-indole-5-carboxylateHCID 10942334Sodium MethoxideHCID 178513189HCID 178513189, compound

Product 1

HCID 57263143HCID 57263143, compoundYield 8.8%

Conditions

Temperature
60 °C

Procedure

To a stirred solution of NaOMe [prepared in-situ from sodium metal (0.261 g, 11.36 mmol) in MeOH (10 mL) at 60° C.] was added hydroxyguanidine (0.863 g, 11.36 mmol) and the resulting mixture was stirred at 60° C. for 30 min. To the above mixture, methyl 1H-indole-5-carboxylate (1 g, 5.68 mmol) was added and the reaction was stirred at 60° C. for 12 h. The reaction was cooled to RT and quenched with H2O (100 mL). The aqueous layer was extracted in EtOAc (2×100 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by triturating with pentane to give 5-(1H-indol-5-yl)-[1,2,4]oxadiazol-3-ylamine (0.1 g, 8.6%) as an off-white solid. MS (ESI, pos. ion) m/z: 201.1 (M+1). 1H-NMR (400 MHz DMSO-d6): δ 11.53 (s, —1H), 8.24 (s, 1H), 7.73 (dd, J=11.6, 2.4 Hz, 1H), 7.56 (m, 2H), 6.61 (s, 1H), 6.29 (s, 2H).

Workup

  1. stirringthe reaction was stirred at 60° C. for 12 h
  2. temperatureThe reaction was cooled to RT
  3. customquenched with H2O (100 mL)
  4. extractionThe aqueous layer was extracted in EtOAc (2×100 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified
  8. customby triturating with pentane

Sources & evidence

ORD record
ord-c71fe6e77d92463fb97be40b2ea264fb
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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