Ammonium Chloride → 1H-Indole-2-carboxamide

HRID 62646

Reaction equation

HRID 62646 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.CC[N:15](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-]>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]([NH2:15])=[O:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 72899Indole-2-carboxylic acidHCID 81531DiisopropylethylamineHCID 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 a solution of indole-2-carboxylic acid (1e: 1 mmol) in DMF (4 mL) was added DIPEA (2 eq.) followed by HATU (1.2 eq.). The mixture was stirred for 15 minutes before the desired amine (R6—NH2) was added. The mixture was left to stir at room temperature for 5-16 hrs before saturated NH4Cl solution was added. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude material was purified on CombiFlash® purification system (Teledyne Isco) using appropriate mixtures of ethyl acetate and cyclohexanes to obtain the desired product indole-2-carboxamide (I).

Workup

  1. additionwas added
  2. waitThe mixture was left
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined organic extracts were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified on CombiFlash® purification system (Teledyne Isco)

Sources & evidence

ORD record
ord-3464dd8d004140eca2db07302f7e781e
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Linked notes

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