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

HRID 733658Notes

Reaction equation

HRID 733658 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]2[NH:9][CH:10]=[C:11]([CH3:12])[C:3]=12.[H-].[Na+].FC(F)(F)S(O[Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])(=O)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]2[N:9]([Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:10]=[C:11]([CH3:12])[C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 578409124-bromo-7-chloro-3-methyl-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 578410424-Bromo-1-(tert-butyl-dimethyl-silanyl)-7-chloro-3-methyl-1H-pyrrolo[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-7-chloro-3-methyl-1H-pyrrolo[2,3-c]pyridine (1.07 g) in dry tetrahydrofuran (50 ml) at 0° C. under an atmosphere of nitrogen was added portionwise sodium hydride (60% dispersed in mineral oil, 384 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 (2 ml) in dry tetrahydrofuran (10 ml) was added dropwise. The solution was stored at 5° C. overnight. The solution was partitioned between ethyl acetate and water and washed with water twice. The organic layer was dried (MgSO4) and evaporated to give a brown oil (2 g). The residue was used in the next step (d) without further purification.

Workup

  1. additionAfter addition
  2. customwas then recooled to 0° C.
  3. waitThe solution was stored at 5° C. overnight
  4. customThe solution was partitioned between ethyl acetate and water
  5. washwashed with water twice
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-b0eb9f5509bf44d79603e8b62a12fc60
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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