HCID 11396572, compound → HCID 57732795, compound

HRID 562020Notes

Reaction equation

HRID 562020 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]>C1COCC1.O=[Mn]=O>[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]=[O:28])=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 1

HCID 11396572HCID 11396572, compound

Product 1

HCID 57732795HCID 57732795, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[4-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide (25 mg, 0.058 mmol) in THF (5 mL), MnO2 (160.0 mg, 1.73 mmol) was added at ambient temperature. The resulting suspension was stirred overnight, filtered through celite, and the solid rinsed with THF (3×10 mL). The filtrate was concentrated to give the title compound (15 mg, 58%) which was used in the next step without purification.

Workup

  1. filtrationfiltered through celite
  2. washthe solid rinsed with THF (3×10 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ff533de6526a438a813f7863d2bbb38e
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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