Hydrochloric Acid → 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

HRID 2199321Notes

Reaction equation

HRID 2199321 reaction equation
[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.[O-:23]Cl=O.[Na+].Cl>O.CC(C)=O>[Cl:1][C:2]1[C:7]([C:8]([OH:23])=[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668197Sodium ChloriteHCID 585570714-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 673458404-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of NaH2PO4.2H2O (513 mg, 3.3 mmol) in water (3 ml), was added a solution of 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (500 mg, 1.50 mmol) in acetone (6 ml) at 0° C. A solution of NaClO2 (541 mg, 5.98 mmol) in water (3 ml) was added to the reaction mixture at 0° C. and the reaction mixture was warmed to room temperature spontaneously. After 2 hours, 1N HCl solution was added to reach pH=5. The produced solid was filtered and dried with nitrogen gas flow. The title product (440 mg, 84% yield) was used next reaction without further purification. MS m/z: 351 [M+1].

Workup

  1. filtrationThe produced solid was filtered
  2. customdried with nitrogen gas flow

Sources & evidence

ORD record
ord-6c772f35675743f68a8a78089094a318
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

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