Triethylamine → 1H-Indole-2-carboxamide

HRID 62644

Reaction equation

HRID 62644 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C[N:14](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:14])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 72899Indole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 5948321H-Indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To indole-2-carboxylic acid (1e) (500 μL, 0.2 M in anhydrous DMF) was added HATU (250 μL, 0.4 M in anhydrous DMF) and Et3N (50 μL, 2.0 M in anhydrous DMF) and stirred for 5 minutes at room temperature. The desired amine (R6—NH2) was dissolved in 520 μL anhydrous DMF and added to the reaction mixture. The reaction mixture was stirred for two hours at 45° C. and the solvent was evaporated in vacuo and the residue was purified via preparative HPLC to obtain the desired product indole-2-carboxamide (I).

Workup

  1. additionadded to the reaction mixture
  2. stirringThe reaction mixture was stirred for two hours at 45° C.
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-e66f91d3cee4486fb48425e2aee0cf67
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Linked notes

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