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

HRID 1969873Notes

Reaction equation

HRID 1969873 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[H-].[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C=O)C>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[CH:11]=[CH:12][C:3]=12

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 585570714-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (2.00 g, 11.1 mmol, Adesis) in DMF (30 mL) was added NaH (60% dispersion in mineral oil, 0.500 g, 12.5 mmol) forming a yellow solution. The reaction mixture was stirred at ambient temperature for about 30 min then 4-methylbenzene-1-sulfonyl chloride (2.40 g, 12.6 mmol) was added. The reaction mixture was stirred at ambient temperature for about 30 min and poured into ice water (about 50 mL). The solid was collected via vacuum filtration, while washing with water (about 15 mL), and dried in a vacuum oven to give 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (3.22 g, 87%) as an off white solid: LC/MS (Table 1, Method b) Rt=2.56 min; MS m/z: 335 (M+H)+.

Workup

  1. customforming a yellow solution
  2. stirringThe reaction mixture was stirred at ambient temperature for about 30 min
  3. filtrationThe solid was collected via vacuum filtration
  4. washwhile washing with water (about 15 mL)
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-68b0ac3569d74c6a8e3728b26b429da3
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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