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

HRID 2199320Notes

Reaction equation

HRID 2199320 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.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[CH:12][C:3]=12

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 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 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (500 mg, 2.78 mmol) in MC (9 mL) were added TsCl (556 mg, 2.91 mmol) and DMAP (509 mg, 4.17 mmol). The reaction mixture stirred for 8 hours at room temperature. The produced precipitated was filtered, washed with water and dried with nitrogen gas flow. The title product (810 mg, 87% yield) was used without further purification. MS m/z: 335 [M+1].

Workup

  1. customThe produced precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried with nitrogen gas flow

Sources & evidence

ORD record
ord-1614806ccaa441148b910cab9f77e112
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

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