Sodium Bicarbonate → HCID 57682777, compound

HRID 494963Notes

Reaction equation

HRID 494963 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH2:32])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:33])[CH:8]=[CH:9][O:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[OH:33][CH:7]1[C:6]2[C:11](=[C:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH2:32])=[O:31])[CH:28]=5)[CH:23]=[CH:22]4)[CH2:17][CH2:16]3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride3×HCID 57682848HCID 57682848, compound

Product 1

HCID 57682777HCID 57682777, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

52 mg of 1-(1-(2-(7-methoxy-4-oxo-4H-chromen-8-yl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamide was dissolved in 6 ml of methanol-tetrahydrofuran (1:1). Thereafter, 5 mg of sodium borohydride was added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature for 2 hours. Thereafter, 5 mg of sodium borohydride was added to the reaction solution, and further, 5 mg each of sodium borohydride was added thereto 2 hours and 4 hours later. Thereafter, the reaction solution was stirred at the same temperature overnight. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with chloroform. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate-methanol), so as to obtain 30 mg of the subject compound.

Workup

  1. temperaturewhile cooling on ice
  2. custom2 hours and 4 hours
  3. stirringThereafter, the reaction solution was stirred at the same temperature overnight
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-7a1a779f7816436aa464b5042d4957b4
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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