Indole-2-carboxylic acid → HCID 86592799, compound

HRID 1372717Notes

Reaction equation

HRID 1372717 reaction equation
CCN=C=NCCCN(C)C.Cl.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]([OH:24])=O.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:28][C:27]=1[O:40][CH3:41].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])=[CH:28][C:27]=1[O:40][CH3:41])=[O:24]

Participants

8

Reactant 4

HCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22244730HCID 22244730, compound

Product 1

HCID 86592799HCID 86592799, compoundYield 55.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In DMF (10 ml), EDC HCl (1.43 g, 7.45 mmol) was added to indole-2-carboxylic acid (1.00 g, 6.21 mmol), tert-butyl 4-amino-3-methoxyphenylacetate (1.47 g, 6.21 mmol), HOBt (0.42 g, 3.10 mmol), and DMAP (0.38 g, 3.10 mmol). The resulting mixture was stirred at 60° C. for 16 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane:ethyl acetate (1:1, v/v) eluate fractions, tert-butyl (4-((2-indolylcarbonyl)amino)-3-methoxyphenyl)acetate (1.31 g, 55%) was obtained as a brown solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane:ethyl acetate (1:1

Sources & evidence

ORD record
ord-83efe765cc8e4269bc85f418d52dce49
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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