4-Fluorobenzaldehyde → HCID 67231029, compound

HRID 1511962Notes

Reaction equation

HRID 1511962 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:15])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([N:15]=[CH:21][C:20]2[CH:23]=[CH:24][C:17]([F:16])=[CH:18][CH:19]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 67086290HCID 67086290, compound

Product 1

HCID 67231029HCID 67231029, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-amino-1H-indole-2-carboxylic acid ethyl ester (1.48 g) and 4-fluorobenzaldehyde (1.55 mL) in ethanol (20 mL) was refluxed for 1 h. TLC showed complete reaction, the mixture was directly used in the next step. An aliquot (20 micro liters) of the reaction mixture was taken and concentrated for the NMR analysis. 1H NMR (CDCl3, δ in ppm): 8.52 (s, 1H), 7.95 (m, 2H), 7.63 (m, 2H), 7.35 (m, 2H), 7.17 (m, 4H), 4.35 (q, 2H, J=7.0 Hz), 1.36 (t, 3H, J=7.0 Hz).

Workup

  1. temperaturewas refluxed for 1 h
  2. customreaction
  3. concentrationconcentrated for the NMR analysis

Sources & evidence

ORD record
ord-452919d86e9b42b594f4d41fe1f08da2
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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