Sodium Sulfite → 6-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carboxylic acid

HRID 1054760Notes

Reaction equation

HRID 1054760 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1.P([O-])(O)(O)=[O:24].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(=CC)C.C(O)(C)(C)C.O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:24])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866987526-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carbaldehyde

Product 1

HCID 866987536-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carboxylic acidYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 230840282-Methyl-2-butene t-butanol waterSolvent

Procedure

To 6-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carbaldehyde (40 mg, 0.13 mmol) in 2-methyl-2-butene/t-butanol/water (v/v/v=1/1/1, 6 mL) was added sodium dihydrogen phosphate (30.5 mg, 0.254 mmol) and sodium chlorite (23 mg, 0.25 mmol) at room temperature. The resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was added sodium sulfite (0.254 mmol), diluted with water, extracted with EtOAc, then concentrated in vacuo and purified via preparative HPLC to give the title compound (6.0 mg, 14% yield).

Workup

  1. extractionextracted with EtOAc
  2. concentrationconcentrated in vacuo
  3. custompurified via preparative HPLC

Sources & evidence

ORD record
ord-57ca515a1c2d4a23a14ae3dff608bb0f
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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