3,4-Dimethylaniline → 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (3,4-dimethylphenyl)-amide

HRID 1514937Notes

Reaction equation

HRID 1514937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]([OH:20])=O)[CH:12]=2.[CH3:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[CH3:29])[NH2:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH3:21][C:22]1[CH:23]=[C:24]([NH:25][C:18]([C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:9]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])[NH:10]3)=[CH:15][CH:14]=2)=[O:20])[CH:26]=[CH:27][C:28]=1[CH3:29]

Participants

6

Reactant 4

HCID 72483,4-DimethylanilineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669660532-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid

Product 1

HCID 669655772-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (3,4-dimethylphenyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (150 mg, 490 μmol), 3,4-dimethylaniline (60 mg, 500 μmol), HATU (280 mg, 740 μmol), and triethylamine (137 μL, 99 mg, 980 μmol) in DMF (10 mL) was stirred 18 h at ambient temperature. The solution was decanted into ethyl acetate and extracted once with water and five times with brine, then dried, filtered, and the solvent removed under reduced pressure to leave an oil, which was purified by chromatography using a gradient of 10-50% heptane/ethyl acetate to give 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (3,4-dimethylphenyl)-amide. 1H NMR (CDCl3, 400 MHz) δ 8.53 (s, broad, 1H), 8.11 (s, 1H), 7.83 (s, 1H), 7.75 (d, J=8.2 Hz, 1H), 7.58 (d, J=8.3 Hz, 1H), 7.46 (m, 3H), 7.38 (dd, J=10.4, 2.1 Hz, 1H), 7.31 (m, 1H), 7.13 (d, J=8.2 Hz, 1H), 6.72 (s, 1H), 2.29 (s, 3H), 2.25 (s, 2H). MS (m/z) 409.1 (M+1); retention time=1.68 min (Method 10). High Resolution, MS (M+H): theory, 409.0874; measured 409.0867.

Workup

  1. customThe solution was decanted into ethyl acetate
  2. extractionextracted once with water and five times with brine
  3. customdried
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto leave an oil, which
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-ac574a5acf324628a3eb38ec4f7ba19a
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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