tert-Butyldimethylsilyl chloride → 1H-Pyrrolo[2,3-B]pyridine, 4-chloro-1-[(1,1-dimethylethyl)dimethylsilyl]-

HRID 1869186Notes

Reaction equation

HRID 1869186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Li]CCCC.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C1COCC1>[C:19]([Si:16]([CH3:18])([CH3:17])[N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([Cl:1])=[C:3]2[CH:10]=[CH:9]1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 497590071H-Pyrrolo[2,3-B]pyridine, 4-chloro-1-[(1,1-dimethylethyl)dimethylsilyl]-Yield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a −78° C. solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine (prepared as described in WO03/082289, 1.44 g, 9.47 mmol) in THF (75 ml) was slowly added a 1.4 M solution of n-BuLi in THF (7.4 ml). The resulting mixture was stirred for 10 minutes, and then tert-butyl-dimethylsilyl chloride (1.4 g, 9.47 mmol) was added to the mixture. The reaction mixture was warm to RT overnight and partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 1-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine as a clear oil (2.0 g, 62% yield).

Workup

  1. custompartitioned between H2O and EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-642a57c2a36f47e99bf30823d02be786
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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