2-Methyl-2-butene → HCID 86698783, compound

HRID 338451Notes

Reaction equation

HRID 338451 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:22]#[N:23])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:13]=3)[CH:10]=2)[NH:5][CH:4]=1)=[O:2].CC(=CC)C.Cl([O-])=[O:30].[Na+].O.OP([O-])(O)=O.[Na+].[Cl-].[NH4+]>C1COCC1.C(O)(C)(C)C.O>[C:22]([C:8]1[CH:7]=[C:6]2[C:11]([C:3]([C:1]([OH:30])=[O:2])=[CH:4][NH:5]2)=[CH:10][C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][OH:21])=[CH:16][CH:17]=1)#[N:23]

Participants

9

Reactant 5

HCID 105532-Methyl-2-buteneHCID 25517Ammonium ChlorideHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86698784HCID 86698784, compound

Product 1

HCID 86698783HCID 86698783, compoundYield 7.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 3-formyl-5-[4-(2-hydroxyethoxy)phenyl]-1H-indole-6-carbonitrile (110 mg, assume 0.2 mmol) in a mixture of THF (1.5 mL) and tert-butanol (1.5 mL) was added 2-methyl-2-butene (0.638 mL, 6.0 mmol) followed by a solution of sodium chlorite (169 mg, 2.0 mmol) and sodium phosphate monobasic monohydrate (284 mg, 2.06 mmol) in water (1.1 mL) via glass pipet at room temperature. The mixture was stirred at room temperature for 15.5 hours. The reaction mixture was poured into saturated aqueous ammonium chloride solution (10 mL) and extracted with ethyl acetate (3×8 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in DMSO (1.8 mL) and half of this solution was purified by reverse phase prep-HPLC to give the title compound (5 mg). MS (ES−) 321.1 (M−H)−. Retention time: 0.90 min Waters Xbridge dC18 5 um 4.6×50 mm, 95% H2O/5% MeCN linear to 5% H2O/95% MeCN over 4.0 min, HOLD at 5% H2O/95% MeCN to 5.0 min. (0.03% NH4OH). Flow: 2.0 mL/min.

Workup

  1. extractionextracted with ethyl acetate (3×8 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in DMSO (1.8 mL)
  5. customhalf of this solution was purified by reverse phase prep-HPLC

Sources & evidence

ORD record
ord-2b878490bc464ebf93e46fa7eb0027e2
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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