Potassium Phosphate, Tribasic → [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester

HRID 1784842Notes

Reaction equation

HRID 1784842 reaction equation
[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[CH:10]=[C:9]([C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:8]=[C:7](Br)[CH:6]=1.CC1(C)C(C)(C)OB([C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][N:33]3[Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)C1C=CC=CC=1C1C=CC=CC=1N(C)C>[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[CH:6]=[C:7]([C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][N:33]3[Si:38]([CH:42]([CH3:44])[CH3:43])([CH:45]([CH3:47])[CH3:46])[CH:39]([CH3:40])[CH3:41])[CH:8]=[C:9]([C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:10]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 50994354[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester

Product 1

HCID 50994359[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl esterYield 70.6%

Reagents, catalysts & solvents 2

HCID 178482708HCID 178482708, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester (316 mg, 0.94 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (0.377 mg, 0.94 mmol) and chloro(di-2-norbornylphosphino)(2′dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (53 mg, 0.094 mmol) were dissolved in dioxane (6 mL) under nitrogen. Aqueous 2M K3PO4 (1 mL, 1.2 mmol) was added and the mixture was heated at reflux overnight. The reaction mixture was filtered through Celite® and the solvent was removed. The product was chromatographed to give 0.350 g (70% yield) of [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered through Celite®
  4. customthe solvent was removed
  5. customThe product was chromatographed

Sources & evidence

ORD record
ord-44a512c93d614393a6546052294ee94c
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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