Diethyl Ether → HCID 58565353, compound

HRID 2175317Notes

Reaction equation

HRID 2175317 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:18]=[O:19])[N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:4][CH:3]=1.[CH3:20][Mg]Br.CCOCC>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:18]([OH:19])[CH3:20])[N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58565349HCID 58565349, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58565353HCID 58565353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-chloro-1-(3-fluorophenyl)-1H-indole-2-carbaldehyde (50 mg, 0.18 mmol) in tetrahydrofuran (5 mL) was added 3.0 M methylmagnesium bromide in ether (0.091 mL, 0.27 mmol). The reaction was stirred at room temperature for 1 hour, quenched with water, and then extracted with ethyl acetate (EtOAc). The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give the desired product (51 mg). The crude product was used directly in next step. LCMS calculated for C16H14ClFNO(M+H)+: m/z=290.1. Found: 289.7.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (EtOAc)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0489c29f40c94f4faade14fec37b3a75
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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