P-Anisidine → HCID 11620261, compound

HRID 735807Notes

Reaction equation

HRID 735807 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:4]=[C:3]1[C:18]([OH:20])=O.CCN([CH:27]([CH3:29])[CH3:28])C(C)C.CN(C(O[N:38]1N=N[C:40]2[CH:41]=[CH:42][CH:43]=[N:44][C:39]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:54]1C=NC2N(O)N=NC=2C=1.C[O:65][C:66]1[CH:71]=[CH:70]C(N)=CC=1.C[CH2:74][O:75][C:76](C)=O>CN(C=O)C>[C:27]([C:41]1[CH:40]=[C:39]([N:38]2[CH2:70][CH2:71][C:66]2=[O:65])[C:74]([O:75][CH3:76])=[C:43]([NH:44][C:18]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][C:9]=3[O:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[O:20])[CH:42]=1)([CH3:29])([CH3:54])[CH3:28]

Participants

8

Reactant 6

HCID 7732P-AnisidineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22025245HCID 22025245, compound

Product 1

HCID 11620261HCID 11620261, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-methyl-7-(pyridine-4-yloxy)-1H-indole-2-carboxylic acid (40 mg, 0.15 mmol) in DMF (1 mL) was added Hunig's base (52 microL, 0.3 mmol) resulting in a clear solution. After 5 min, HATU (90 mg, 0.23 mmol) and HOAT (3 mg, 0.02 mmol) were added followed by the above anisidine (37 mg, 0.15 mmol). The mixture was stirred overnight. The reaction mixture was diluted with EtOAc (30 mL), washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (eluting with 30-80% EtOAc in hexane) to give the title compound (50 mg, 75%).

Workup

  1. customresulting in a clear solution
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (eluting with 30-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-979e319fab52413da04e47291cbe50f5
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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