4-Toluenesulfonyl chloride → ethyl 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1969858Notes

Reaction equation

HRID 1969858 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[CH:15][C:3]=12.[H-].[Na+].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>CN(C=O)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH:14]=[CH:15][C:3]=12

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 58557443ethyl 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylateYield 102.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.32 g, 5.88 mmol) in DMF (39 mL) at about 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.400 g, 10.00 mmol) and the reaction mixture was stirred at this temperature for about 15 min. A solution of 4-methylbenzene-1-sulfonyl chloride (2.24 g, 11.8 mmol) in DMF (17 mL) was added dropwise and the reaction mixture was allowed to warm to ambient temperature for about 2 h. The reaction mixture was concd under reduced pressure and the residue was partitioned between EtOAc and water (25 mL each). The aqueous layer was extracted with EtOAc (2×25 mL) and the combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The solid was triturated with heptane, and the precipitates were filtered to give ethyl 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.28 g, 102%, 90% purity) as a white solid: LCMS (Table 1, Method c) Rt=1.64 min; MS m/z: 379 (M+H)+.

Workup

  1. customthe residue was partitioned between EtOAc and water (25 mL each)
  2. extractionThe aqueous layer was extracted with EtOAc (2×25 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe solid was triturated with heptane
  7. filtrationthe precipitates were filtered

Sources & evidence

ORD record
ord-6a1e38295e744eefb86f96e630873547
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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