Dimethylformamide → HCID 59314118, compound

HRID 1047924Notes

Reaction equation

HRID 1047924 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19](C#N)[C:18]=2C)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].CN([CH:30]=[O:31])C.[C:32]([O-])([O-])=O.[K+].[K+].BrC[C:40]#[N:41]>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:32])[C:18]=2[O:31][CH2:30][C:40]#[N:41])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 59314291HCID 59314291, compound

Product 1

HCID 59314118HCID 59314118, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 30 mL reaction vial is charged with 2-(2-hydroxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (3, 400 mg, 1.18 mmol) and dry DMF (5 mL). A stirring bar is added and stirring is initiated. After dissolution, K2SO4 (326 mg, 2.36 mmol) and bromoacetonitrile (164 μL, 2.36 mmol) are added in turn. The reaction vial is capped and placed in a heating block which is set atop of an orbital shaker. The heating block is set at 55° C. After 16 h, tlc analysis (silica, 1:1 EtOAc in heptanes) indicates that the starting material is completely consumed. Heating is terminated. After sitting at ambient temperature for 1 day, the contents of the flask are filtered through a pad of Celite. The filtrate is transferred to a reparatory funnel which contains EtOAc (40 mL). The layers are separated. The organic phase is washed with water (20 mL), saturated aqueous NaHCO3 and brine (20 mL), and then dried over MgSO4, filtered and concentrated by pumping to constant weight to give dark brown solid (0.42 g). This material is dissolved in 10 mL of DCM. This material is purified utilizing an ISCO Companion with a 25 g cartridge of silica. The gradient is 10% EtOAc in heptanes over 3 column volumes followed by a linear gradient to 50% EtOAc in heptanes over 10 column volumes. 17 mL fractions of eluent are collected. Fractions 4 through 6 are combined and evaporated in vacuo. This provides white solid (0.26 g, 58%).

Workup

  1. customA 30 mL reaction
  2. additionA stirring bar is added
  3. additionare added in turn
  4. customThe reaction
  5. customvial is capped
  6. customis set at 55° C
  7. customis completely consumed
  8. temperatureHeating
  9. customis terminated
  10. waitAfter sitting at ambient temperature for 1 day
  11. filtrationthe contents of the flask are filtered through a pad of Celite
  12. customThe filtrate is transferred to a reparatory funnel
  13. customThe layers are separated
  14. washThe organic phase is washed with water (20 mL), saturated aqueous NaHCO3 and brine (20 mL)
  15. dry with materialdried over MgSO4
  16. filtrationfiltered
  17. concentrationconcentrated

Sources & evidence

ORD record
ord-48e54feb87a24d88ba834d26109451d5
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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