Cesium carbonate → tert-butyl 1-(1-cyclopropyl-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 2206597Notes

Reaction equation

HRID 2206597 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[CH:19]([CH3:25])[C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:22]1([C:20](=[O:21])[CH:19]([N:10]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:2]2[CH3:1])[CH3:25])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 450808052-Bromo-1-cyclopropylpropan-1-oneHCID 89739113tert-Butyl 2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 117778856tert-butyl 1-(1-cyclopropyl-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of tert-butyl 2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (300.00 mg, 1.29 mmol), 2-bromo-1-cyclopropylpropan-1-one (342.98 mg, 1.94 mmol), Cs2CO3 (841.63 mg, 2.58 mmol), KI (42.88 mg, 0.26 mmol) in DMF (4 ml) were stirred at 25° C. for 18 h. After the reaction completed, the solution was partitioned between EtOAc and H2O. The organic layer was separated, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by flash column (Eluent: PE:EtOAc=10:1) to get tert-butyl 1-(1-cyclopropyl-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate as a white oil. (230 mg, yield 54%).

Workup

  1. customthe solution was partitioned between EtOAc and H2O
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash column (Eluent: PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-7abc3c676d4348d3a84799ca4c0ac5aa
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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