2-Methyl-2-butene → Sodium chlorite sodium dihydrogen phosphate

HRID 1054790Notes

Reaction equation

HRID 1054790 reaction equation
[Cl:1]([O-:3])=[O:2].[Na+:4].[P:5]([O-:9])([OH:8])([OH:7])=[O:6].[Na+].[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]([CH:21]=[O:22])=[CH:17][NH:18]2)=[CH:14][C:13]=1[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][OH:31])=[C:25]([O:32][CH3:33])[CH:24]=1.CC(=CC)C.S([O-])([O-])=[O:40].[Na+].[Na+]>O.C(OCC)(=O)C.C(O)(C)(C)C.C1COCC1>[Cl:1]([O-:3])=[O:2].[Na+:4].[P:5]([O-:9])([OH:8])([OH:7])=[O:6].[Na+:4].[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:21]([OH:40])=[O:22])=[CH:17][NH:18]2)=[CH:14][C:13]=1[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][OH:31])=[C:25]([O:32][CH3:33])[CH:24]=1

Participants

11

Reactant 5

HCID 105532-Methyl-2-buteneHCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866987776-Chloro-5-(4-(2-hydroxyethyl)-3-methoxyphenyl)-1h-indole-3-carbaldehyde

Product 2

HCID 86629097Sodium chlorite sodium dihydrogen phosphateHCID 866987786-chloro-5-[4-(2-hydroxyethyl)-3-methoxyphenyl]-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 2.5 M/2.65 M of sodium chlorite/sodium dihydrogen phosphate in water was prepared and 1.0 mL (2.5 mmol sodium chlorite and 2.6 mmol sodium dihydrogen phosphate) was added to a vial containing 6-chloro-5-[4-(2-hydroxyethyl)-3-methoxyphenyl]-1H-indole-3-carbaldehyde, 1.0 mL THF, 0.5 mL t-butanol, 0.5 mL 2-methyl-2-butene, and sealed then heated to 30° C. for 3 hours. Sodium sulfite (315 mg, 2.50 mmol) was then added and the mixture stirred for 15 min. Ethyl acetate was then added to extract (3×1 mL). The organic layer was separated and solvents removed by speedvac. The residue was purified by reverse phase HPLC to give the title compound. MS(AP−) 344 (M−H)−. Retention time=1.892 Column Xbridge C18 2.1×50 mm 5 μm, Temperature 50° C. Mobile Phase A=0.05% NH4OH in water. Mobile Phase B=100% acetonitrile. Gradient: Initial 5% B Time 0.00 mins, 5% B Time 0.50 mins, 5% B Time 3.40 mins, 100% B Time 4.20 mins, 100% B Time 4.21 mins, 5% B Time 4.70 mins, 5% B Flow rate, 0.8 mL/min Injection volume 2 μL. Agilent 1200 HPLC/1956 MSD/SEDEX 75 ELSD Ionization Mode API-ES Polarity Negative

Workup

  1. customsealed
  2. extractionto extract (3×1 mL)
  3. customThe organic layer was separated
  4. customsolvents removed by speedvac
  5. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d516c7a18d654b9d9d7849ec4e364921
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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