2-Methyl-2-butene → 5-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carboxylic acid

HRID 1054658Notes

Reaction equation

HRID 1054658 reaction equation
[OH:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][C:20]=3[CH3:21])[NH:17][CH:16]=[C:15]4[CH:22]=[O:23])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.CC(=CC)C.Cl([O-])=[O:30].[Na+].O.OP([O-])(O)=O.[Na+].[Cl-].[NH4+]>O1CCCC1.C(O)(C)(C)C.O>[OH:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][C:20]=3[CH3:21])[NH:17][CH:16]=[C:15]4[C:22]([OH:30])=[O:23])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1

Participants

9

Reactant 5

HCID 105532-Methyl-2-buteneHCID 25517Ammonium ChlorideHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 866986615-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 866986625-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A partial suspension of 5-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carbaldehyde (130 mg, 0.426 mmol) in tetrahydrofuran (3 mL) and tert-butanol (3 mL) was treated with 2-methyl-2-butene (2.27 mL, 21.4 mmol) followed by a solution of sodium chlorite (538 mg, 6.4 mmol) and sodium phosphate monobasic hydrate (904 mg, 6.5 mmol) in water (2 mL) via glass pipet at room temperature. The reaction mixture was stirred vigorously at room temperature for 62 hours, and was poured into half-diluted saturated aqueous ammonium chloride solution (50 mL). The product was extracted with ethyl acetate (3×60 mL), and the combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified using reverse-phase chromatography to give the title compound.

Workup

  1. extractionThe product was extracted with ethyl acetate (3×60 mL)
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-10dc6b922c2c4b17b9229c5202338e88
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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