2-Methyl-2-butene → HCID 71767832, compound

HRID 338256Notes

Reaction equation

HRID 338256 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]([C:19]2([OH:23])[CH2:22][CH2:21][CH2:20]2)=[CH:15][C:14]=1[F:24].Cl([O-])=[O:26].[Na+].O.OP([O-])(O)=O.[Na+].CC(=CC)C>C(#N)C.C(O)(C)(C)C.O>[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:18]=[CH:17][C:16]([C:19]2([OH:23])[CH2:22][CH2:21][CH2:20]2)=[CH:15][C:14]=1[F:24]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86698602HCID 86698602, compound

Product 1

HCID 71767832HCID 71767832, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 6-chloro-5-[2-fluoro-4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carbaldehyde (57 mg, 0.17 mmol) in acetonitrile (1 mL) and tert-butanol (1 mL) was added a solution of sodium chlorite (112 mg, 1.7 mmol), sodium phosphate monobasic hydrate (199 mg, 1.7 mmol) in water (2 mL) and 2-methyl-2-butene (0.72 mL, 6.8 mmol). The mixture was stirred at room temperature for 24 hours. The mixture was concentrated in vacuo and treated with ethanol. The solids were filtered and the filtrate was concentrated in vacuo to give crude product, which was purified using reverse phase chromatography to give the title compound (12 mg, 20%). MS (ES+) 360.057 (M+H)+. Retention time: 2.60 min. Column: Waters Atlantis dC18 4.6×50 mm, 5 μm. Modifier: TFA 0.05%. Gradient: 95% H2O/5% MeCN linear to 5% H2O/95% MeCN over 4.0 min, HOLD at 5% H2O/95% MeCN to 5.0 min. Flow: 2.0 mL/min.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiontreated with ethanol
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto give crude product, which
  6. customwas purified

Sources & evidence

ORD record
ord-c4aeced7e67c446da3f599edeeff4fd9
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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