Cesium carbonate → methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

HRID 2170990Notes

Reaction equation

HRID 2170990 reaction equation
S([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[CH:13]=[C:12]1[C:20]([O:22][CH2:23]C)=[O:21])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CO.C1COCC1>[NH:11]1[C:15]2[N:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[C:12]1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 67975542ethyl 1-tosyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Product 1

HCID 17390026methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of compound 6-c (6 g, 17.4 mmol) and Cs2CO3 (CAS 534-17-8) (17 g, 52.2 mmol) in methanol (70 mL) and THF (140 mL) was stirred at 15° C. for 12 h. The solvent was removed under vacuum. H2O (30 mL) was added and the mixture was extracted with ethyl acetate (30 mL×3). The organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated under vacuum to yield product 6-d as a white powder (1.39 g, 46%).

Workup

  1. customThe solvent was removed under vacuum
  2. additionH2O (30 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated under vacuum
  7. customto yield product 6-d as a white powder (1.39 g, 46%)

Sources & evidence

ORD record
ord-609da277a94f4195bddf1f70119c52ec
Source dataset
uspto-grants-2015_06
Patent number
US09051317B2

Reaction notes

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