Cesium carbonate → HCID 86619739, compound

HRID 1921220Notes

Reaction equation

HRID 1921220 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:13]=[N:12][C:11]([Cl:14])=[C:10]2[NH:15][CH:16]=[C:17]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:9]=12.Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CN(C=O)C>[Br:7][C:8]1[CH:13]=[N:12][C:11]([Cl:14])=[C:10]2[N:15]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:16]=[C:17]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:9]=12

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 86619740HCID 86619740, compound

Product 1

HCID 86619739HCID 86619739, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (185 mg, 0.568 mmol) was added to a solution of methyl (4-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridin-3-yl)acetate from Step C (115 mg, 0.379 mmol) and tert-butyl bromoacetate (0.0810 mL, 0.417 mmol) in DMF (2 mL). After 30 min, the mixture was partitioned between H2O (5 mL) and EtOAc (10 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=419 (M+1).

Workup

  1. customthe mixture was partitioned between H2O (5 mL) and EtOAc (10 mL)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-927cd890ee46472493f92b7955d72af6
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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