Methyl Anthranilate → HCID 69354171, compound

HRID 1827463Notes

Reaction equation

HRID 1827463 reaction equation
Cl[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[CH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2C2C=CC=CC=2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:54]([O:63][CH3:64])(=[O:62])[C:55]1[C:56](=[CH:58][CH:59]=[CH:60][CH:61]=1)[NH2:57]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:64][O:63][C:54](=[O:62])[C:55]1[CH:61]=[CH:60][CH:59]=[CH:58][C:56]=1[NH:57][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[CH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8635Methyl AnthranilateHCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 693535806-Chloro-3-[2-(5-ethyl-pyridin-2-yl)-vinyl]-1H-indazole

Product 1

HCID 69354171HCID 69354171, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

1,2-Dimethoxymethane (2 mL) was added to 6-Chloro-3-[2-(5-ethyl-pyridin-2-yl)-vinyl]-1H-indazole (130 mg, 0.354 mmol), tris(dibenzylideneacetone)dipalladium (16 mg, 0.018 mmol), -(dicyclohexylphosphino)biphenyl (25 mg, 0.071 mmol), K3PO4 (0.188 g, 0.885 mmol), and methyl anthranilate (0.092 mL, 0.71 mmol). The reaction was vacuum flushed with argon (4×) and then heated to 80 degrees Celsius for 19 hours. The reaction was diluted with EtOAc (20 mL) and filtered through a silica gel plug. After washing with EtOAc (50 mL), the solvent was removed by rotary evaporation. The crude oil was purified by chromatography (40 g silica gel, 30–40% EtOAc/hexanes) to yield the desired product (54 mg, 32%).

Workup

  1. customflushed with argon (4×)
  2. temperatureheated to 80 degrees Celsius for 19 hours
  3. additionThe reaction was diluted with EtOAc (20 mL)
  4. filtrationfiltered through a silica gel plug
  5. washAfter washing with EtOAc (50 mL)
  6. customthe solvent was removed by rotary evaporation
  7. customThe crude oil was purified by chromatography (40 g silica gel, 30–40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-87bd7c8a6eab41f198ca2bbd5be35802
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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