Sodium Chlorite → HCID 86698768, compound

HRID 338436Notes

Reaction equation

HRID 338436 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-f8ab33932e3d44f49d9df08a3d3d6b26
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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