Chloromethyl pivalate → HCID 10429031, compound

HRID 1376129Notes

Reaction equation

HRID 1376129 reaction equation
[K+].[N:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:18]([O-:20])=[O:19])=[CH:4][CH:3]=1.Cl[CH2:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[CH3:26][C:25]([CH3:28])([CH3:27])[C:24]([O:23][CH2:22][O:19][C:18]([C:10]1[NH:11][C:12]2[C:17]([C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:20])=[O:29]

Participants

4

Reactant 2

HCID 87885Chloromethyl pivalateHCID 690066653-(4-Pyridinylamino)-1h-indole-2-carboxylic acid potassium salt

Product 1

HCID 10429031HCID 10429031, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Stir at 50° C. a mixture of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid potassium salt (1.0 g, 3.43 mmol), KI (0.16 g) 2,2-dimethyl-propionic acid chloromethyl ester (0.63 g, 4.16 mmol) in DMF (20 mL) for 1.5 h. Cool, and partition between H2O-EtOAc. Wash the extract with aqueous NaHCO3 solution, dry the extract (MgSO4), filter and concentrate under vacuum to afford the crude product. Chromatography the product on a silica gel column eluting with 8% MeOH/EtOAc to obtain 0.64 g of the title compound as a solid; MS 326(M+H), m.p. 223–224° C. TLC (silica gel, 8% MeOH/EtOAc) Rf=0.30.

Workup

  1. temperatureCool
  2. custompartition between H2O-EtOAc
  3. washWash the
  4. extractionextract with aqueous NaHCO3 solution
  5. customdry the
  6. extractionextract (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate under vacuum
  9. customto afford the crude product
  10. washChromatography the product on a silica gel column eluting with 8% MeOH/EtOAc

Sources & evidence

ORD record
ord-31edc5e4e5d94e1290696f28a6027592
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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