Sodium hydride → 4-Bromo-1-(tert-butyl-dimethyl-silanyl)-7-chloro-1H-pyrrolo[2,3-c]pyridine

HRID 733677Notes

Reaction equation

HRID 733677 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[H-].[Na+].FC(F)(F)S(O[Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])(=O)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]2[N:9]([Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:10]=[CH:11][C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 110317234-Bromo-7-chloro-1H-pyrrolo(2,3-c)pyridine

Product 1

HCID 578410104-Bromo-1-(tert-butyl-dimethyl-silanyl)-7-chloro-1H-pyrrolo[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine (1.64 g) in dry tetrahydrofuran (80 ml) at 0° C. under an atmosphere of nitrogen was added portionwise sodium hydride (60% dispersion in mineral oil, 625 mg). After addition, the solution was stirred at room temperature for 30 minutes. The solution was then recooled to 0° C. and a solution of tert-butyldimethylsilyl trifluoromethanesulphonate (3.75 g) in dry tetrahydrofuran (20 ml) was added dropwise. The solution was partitioned between ethyl acetate (100 ml) and water (100 ml) and washed with water until the pH of the aqueous was neutral. The organic layer was dried (MgSO4) and evaporated to give a brown oil. The residue was purified by Biotage chromatography over silica gel (10 g), eluting with 10% ethyl acetate/isohexane to give the title compound as a red oil. (1.63 g).

Workup

  1. additionAfter addition
  2. customwas then recooled to 0° C.
  3. customThe solution was partitioned between ethyl acetate (100 ml) and water (100 ml)
  4. washwashed with water until the pH of the
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customto give a brown oil
  8. customThe residue was purified by Biotage chromatography over silica gel (10 g)
  9. washeluting with 10% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-a04213d921c342c888d05101cde38aa9
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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