Hydrochloric Acid → HCID 66738037, compound

HRID 1640914Notes

Reaction equation

HRID 1640914 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[CH:16]=[O:17])[C:2]1=2.[CH3:18][Mg]Br.Cl.[OH-].[NH4+]>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[CH:16]([OH:17])[CH3:18])[C:2]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86641875HCID 86641875, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66738037HCID 66738037, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 4-benzo[b]thiophen-7-yl-pyridine-3-carbaldehyde (1.5 g, 6.27 mmol in THF (50 mL) in a 250-mL round bottom flask to 0° C. and add gradually methylmagnesium bromide (2.38 g, 6.90 mmol, 2.30 mL) to the solution. Stir the mixture from 0° C. to RT for 2 h. Hydrolyze the mixture by mixing with 1 N HCl (200 mL). Adjust the pH to 11 with ammonium hydroxide. Extract into chloroform/IPA (3/1, 200 mL). Wash the organic phase with water and saturated aqueous sodium chloride. Dry over sodium sulfate and concentrate in vacuo. Purify by FCC (hexane to 10% ethyl acetate in hexane, then 20% THF in DCM) to give the title compound as a yellow oil (1.00 g, 62%). MS (ES) m/z 256 [M+1]+.

Workup

  1. extractionExtract into chloroform/IPA (3/1, 200 mL)
  2. washWash the organic phase with water and saturated aqueous sodium chloride
  3. dry with materialDry over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. customPurify by FCC (hexane to 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6febb96262c045eba7cc41ea0b732c8d
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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