Dimethylformamide → Methyl 3-formyl-1H-indole-5-carboxylate

HRID 1666844Notes

Reaction equation

HRID 1666844 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)=[O:9].CN([CH:22]=[O:23])C>>[CH:22]([C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:8]([O:7][CH3:6])=[O:9])[CH:11]=2)[NH:15][CH:14]=1)=[O:23]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 19606277Methyl 3-formyl-1H-indole-5-carboxylate

Procedure

Place anhydrous DMF (25 mL) in a flask under an atmosphere of nitrogen, cool to 10° C. and treat dropwise with POCl3 (8.22 g, 54 mmol) while keeping the temperature below 15° C. Add a solution of 5-methoxycarbonyl-1H-indole in 30 mL DMF portionwise keeping the temperature below 20° C. Remove the cooling bath and stir the mixture at ambient temperature for 1 hour then pour onto ice. Addition of 50 mL 5 N NaOH precipitated a solid which is filtered and rinsed with water and EtOAc to give the title compound: 1H NMR (DMSO-d6) 9.95 (s, 1H), 8.76 (s, 1H), 8.4 (s, 1H), 7.9-7.8 (m, 1H), 7.5-7.7 (d, 1H), 3.85 (s, 3H), 1.7 (s, 1H); ISMS 204 (M+1).

Workup

  1. customthe temperature below 15° C
  2. customthe temperature below 20° C
  3. customRemove the cooling bath
  4. additionthen pour onto ice
  5. additionAddition of 50 mL 5 N NaOH
  6. customprecipitated a solid which
  7. filtrationis filtered
  8. washrinsed with water and EtOAc

Sources & evidence

ORD record
ord-b7c3a1083b44469dad0be7df40cf1bad
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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