Sodium hydride → HCID 71076616, compound

HRID 1774488Notes

Reaction equation

HRID 1774488 reaction equation
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[C:19](Br)[CH:18]=1>C1COCC1.C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:18]=1

Participants

8

Reactant 3

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 38477682-Bromo-isonicotinic acid methyl ester

Product 1

HCID 71076616HCID 71076616, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triisopropylsilane-thiol (97%, 1.29 mL, 6.0 mmol) in THF (15 mL) was cooled to 0° C. and then sodium hydride (60% in mineral oil, 0.240 g, 6.0 mmol) was added. After 15 minutes, 2-bromo-isonicotinic acid methyl ester (1 g, 4.6 mmol) in toluene was added and the mixture was purged with N2 (g). Tetrakis(triphenylphosphine)palladium(0) (0.531 g, 4.6 mmol) was added and the reaction was heated to reflux. After cooling the reaction was diluted with EtOAc then washed with H2O and brine. The organic portion was dried and concentrated to afford the title compound, which was used in the next step without further purification.

Workup

  1. customthe mixture was purged with N2 (g)
  2. temperaturethe reaction was heated to reflux
  3. temperatureAfter cooling the reaction
  4. washthen washed with H2O and brine
  5. customThe organic portion was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f0b15c2b1c94445b7aa81a1b13ef0b5
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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