Water → tert-butyl 1-(3-hydroxy-3-methylbutan-2yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 2206564Notes

Reaction equation

HRID 2206564 reaction equation
[CH3:1][C:2]1[N:10]([CH:11]([C:13](=[O:15])[CH3:14])[CH3:12])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH3:23][Mg+].[Br-].O>C1COCC1>[OH:15][C:13]([CH3:23])([CH3:14])[CH:11]([N:10]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[C:2]1[CH3:1])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 89740938HCID 89740938, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 117779158tert-butyl 1-(3-hydroxy-3-methylbutan-2yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of tert-butyl 2-methyl-1-(3-oxobutan-2-yl)-1H pyrrolo[2,3-b]pyridine-3-carboxylate (0.6 g, 2 mmol) in THF (10 mL) were added CH3MgBr (2 mL, 6 mmol) at −78° C. The mixture was stirred at −78° C. for 3 hr. Water (4 mL) was added and the mixture was extracted by ethyl acetate (30 mL*3). The organic layer was washed with brine and dried over sodium sulfate. The crude product was concentrated and purified by pre-TLC (eluted: petroleum ether/ethyl acetate=4/1) to give tert-butyl 1-(3-hydroxy-3-methylbutan-2yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (300 mg, 49%).

Workup

  1. extractionthe mixture was extracted by ethyl acetate (30 mL*3)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe crude product was concentrated
  5. custompurified by pre-TLC (eluted: petroleum ether/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-07f00277097f4d5a9e0430ee0dfadd78
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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