Sodium Chlorite → HCID 86698768, compound

HRID 1054778Notes

Reaction equation

HRID 1054778 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:24]=[CH:23][C:16]2[O:17][C@H:18]([CH2:21][OH:22])[CH2:19][O:20][C:15]=2[CH:14]=1.Cl([O-])=[O:26].[Na+].P([O-])(O)(O)=O.[Na+]>CC(=CC)C.O.C(O)(C)(C)C.C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:26])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:24]=[CH:23][C:16]2[O:17][C@H:18]([CH2:21][OH:22])[CH2:19][O:20][C:15]=2[CH:14]=1

Participants

8

Reactant 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86698767HCID 86698767, compound

Product 1

HCID 86698768HCID 86698768, compoundYield 14.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

A mixture of 6-chloro-5-[(2R)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1H-indole-3-carbaldehyde (1.0 g, 2.9 mmol), sodium chlorite (5.28 g, 58.3 mmol), sodium dihydrogen phosphate (9.06 g, 58.1 mmol) in 2-methyl-2-butene (10 mL), water (10 mL), t-butanol (10 mL) and acetonitrile (10 mL) was stirred overnight at room temperature. The mixture was quenched with saturated aqueous sodium bisulfite. Water (50 mL) and methylene chloride (50 mL) was added. The aqueous layer was extracted with methylene chloride (50 mL×3). The combined organic layer was dried over sodium sulfate, filtered and evaporated to give residue which was purified by reverse phase HPLC to give the title compound (105 mg, 14.3% yield).

Workup

  1. customThe mixture was quenched with saturated aqueous sodium bisulfite
  2. additionWater (50 mL) and methylene chloride (50 mL) was added
  3. extractionThe aqueous layer was extracted with methylene chloride (50 mL×3)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give residue which
  8. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e9022d7fa6af43c88f54b82b3b640700
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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