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

HRID 2206587Notes

Reaction equation

HRID 2206587 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]([C:21](=[O:24])[CH2:22][CH3:23])[CH3:20].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:1][C:2]1[N:10]([CH:19]([C:21](=[O:24])[CH2:22][CH3:23])[CH3:20])[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]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5450922-Bromo-3-pentanoneHCID 89739113tert-Butyl 2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 117778823tert-butyl 2-methyl-1-(3-oxopentan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylateYield 7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The solution of tert-butyl 2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (1.0 g, 4.31 mmol), 2-bromopentan-3-one (1.1 g, 6.46 mmol), Cs2CO3 (2.8 g, 8.61 mmol), KI (142.9 mg, 0.86 mmol) in CH3CN (4 ml) were stirred at 70° C. for 2 h. After the reaction completed, the solution was cooled to r.t. and filtered off. The filtration was evaporated under vacuum. The residue was purified by flash column (Eluent: PE:EtOAc=5:1) to get tert-butyl 2-methyl-1-(3-oxopentan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate as a white oil. (100 mg yield 7%)

Workup

  1. filtrationfiltered off
  2. filtrationThe filtration
  3. customwas evaporated under vacuum
  4. customThe residue was purified by flash column (Eluent: PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-4937361067d345e5aff5ca75682d537d
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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