Triethylamine → HCID 73990723, compound

HRID 1836659Notes

Reaction equation

HRID 1836659 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.FC(F)(F)S([C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]=[CH:31][NH:32]2)(=O)=O.[CH3:39][O:40][N:41]([CH3:46])[C:42](=[O:45])[CH:43]=[CH2:44].C(N(CC)CC)C>CN(C=O)C.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[NH:32]1[C:33]2[C:29](=[CH:28][CH:36]=[C:35]([CH:44]=[CH:43][C:42]([N:41]([O:40][CH3:39])[CH3:46])=[O:45])[CH:34]=2)[CH:30]=[CH:31]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 294174N-methoxy-N-methylprop-2-enamideHCID 22638821HCID 22638821, compound

Product 1

HCID 73990723HCID 73990723, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Tris(dibenzylideneacetone) dipalladium (45 mg, 0.05 mmol) and tri-o-tolylphosphine (120 mg, 0.20 mmol) were stirred in DMF at room temperature for 30 min. The 4-trifluoromethanesulfonyl-1H-indole, N-methoxy-N-methyl acrylamide (1.26 g, 11.00 mmol), and triethylamine (2.20 g, 22.00 mmol) were added and the reaction was heated to 120° C. for 4 h. The reaction was allowed to cool and the solvent removed in vacuo. The residue was taken up in methylene chloride, washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give a brown solid. The solid was purified by flash chromatography (EtOAc, hexanes) to give 3-(1H-indol-6-yl)-N-methoxy-N-methyl-acrylamide (0.90 g, 39% yield for the three reactions). 1H NMR (CDCl3): δ8.385 (bs, 1H), 7.86 (d, J=18.6 Hz, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.57 (s, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.25 (m, 1H), 7.03 (d, J=18.6 Hz, 1H), 6.55 (m, 1H), 3.78 (s, 3H), 3.32 (s, 3H).

Workup

  1. temperatureto cool
  2. customthe solvent removed in vacuo
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown solid
  8. customThe solid was purified by flash chromatography (EtOAc, hexanes)

Sources & evidence

ORD record
ord-f7e95890e2cd4c359baf1cad75630ef1
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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