Sodium Chlorite → HCID 86698611, compound

HRID 338265Notes

Reaction equation

HRID 338265 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]([CH:19]2[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20]2)=[CH:15][CH:14]=1.Cl([O-])=[O:29].[Na+].O.O.OP([O-])(O)=O.[Na+]>C(#N)C.C(O)(C)(C)C.O.CC(=CC)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:29])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([CH:19]2[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20]2)=[CH:17][CH:18]=1

Participants

8

Reactant 3

HCID 23668197Sodium Chlorite2×HCID 23673460Sodium Phosphate, Monobasic, Dihydrate2×HCID 86698610HCID 86698610, compound

Product 1

HCID 86698611HCID 86698611, compoundYield 44.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 6-chloro-5-{4-[1-(methylsulfonyl)pyrrolidin-3-yl]phenyl}-1H-indole-3-carbaldehyde (120 mg, 0.298 mmol) in acetonitrile (5 mL) and tert-butanol (5 mL) was added 2-methyl-2-butene (4 mL). The reaction mixture was cooled to 0° C. and treated with a solution of sodium chlorite (299.5 mg, 3.29 mmol) and sodium phosphate monobasic dihydrate (697 mg, 4.47 mmol) in water (2 mL) dropwise. After the reaction mixture was stirred for 2 h at room temperature, additional sodium chlorite (399.3 mg, 4.39 mmol) and sodium phosphate monobasic dihydrate (930 mg, 5.96 mmol) in H2O (2 mL) and 2-methyl-2-butene (1 mL) was added. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was evaporated in vacuo and the aqueous residue was extracted with EtOAc (3×40 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in DMSO and purified via prep-HPLC to give 6-chloro-5-{4-[1-(methylsulfonyl)pyrrolidin-3-yl]phenyl}-1H-indole-3-carboxylic acid (56 mg) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. customThe reaction mixture was evaporated in vacuo
  3. extractionthe aqueous residue was extracted with EtOAc (3×40 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in DMSO
  7. custompurified via prep-HPLC

Sources & evidence

ORD record
ord-614a0aad5a50447c821f58b436bb70aa
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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