Sodium Formate → HCID 58949905, compound

HRID 1641317Notes

Reaction equation

HRID 1641317 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([CH3:12])[C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.[CH:13]([O-])=[O:14].[Na+]>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>[CH:13]([C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([CH3:12])[C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1)=[O:14]

Participants

4

Reactant 2

HCID 2723810Sodium FormateHCID 58949741HCID 58949741, compound

Product 1

HCID 58949905HCID 58949905, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A 3-neck flask equipped with a condenser and 2 septa was flushed with N2, then the flask was charged with 0.6 g (2.7 mmol) 3-(3-bromophenyl)-2-methylpropionitrile (9-2), 0.275 g (4 mmol) sodium formate, 0.155 g (0.13 mmol) tetrakis(triphenylphosphine)Palladium and flushed with CO from a balloon for 5 min. The solids were suspended in 10 mL DMF and CO continued to bubble into the liquid. The flask was heated in an oil bath at 100′ for 20 min then 110′ while stirring. The color changed from yellow to a deep orange color after 1.5 h, and HPLC/MS analysis showed no starting material and one major product. The reaction was cooled and quenched with brine. The product was extracted into EtOAc, dried over Na2SO4, filtered and concentrated. The product was dissolved in 1 mL CH2Cl2 and purified on an Isco automated system affixed with a Biotage Flash 25(M) cartridge eluted with 0-50% EtOAc in hexane at 25 mL/min over 15 min and hold for 30 min. The product eluted last. MS 174.1 NB#212867-104

Workup

  1. customA 3-neck flask equipped with a condenser
  2. custom2 septa was flushed with N2
  3. customflushed with CO from a balloon for 5 min
  4. customto bubble into the liquid
  5. temperatureThe flask was heated in an oil bath at 100′ for 20 min
  6. customafter 1.5 h
  7. temperatureThe reaction was cooled
  8. customquenched with brine
  9. extractionThe product was extracted into EtOAc
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. dissolutionThe product was dissolved in 1 mL CH2Cl2
  14. custompurified on an Isco automated system
  15. washeluted with 0-50% EtOAc in hexane at 25 mL/min over 15 min
  16. washThe product eluted last

Sources & evidence

ORD record
ord-98a91fce64eb46b5b178ab70421c18d6
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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