HCID 58565348, compound → HCID 58565344, compound

HRID 2175326Notes

Reaction equation

HRID 2175326 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17](N(OC)C)=[O:18])[CH:5]=[CH:6][CH:7]=1.[CH3:23][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17](=[O:18])[CH3:23])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 58565348HCID 58565348, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58565344HCID 58565344, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1-(3-fluorophenyl)-N-methoxy-N-methyl-1H-indole-2-carboxamide (0.30 g, 1.0 mmol) in tetrahydrofuran (6 mL) was added 1.4 M methylmagnesium bromide in tetrahydrofuran (1.1 mL, 1.5 mmol). The reaction was stirred at room temperature for 2 hours, then quenched with saturated NH4Cl solution, extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give the desired product (0.27 g). The crude product was used directly in next step. LCMS calculated for C16H13FNO(M+H)+: m/z=254.1. Found: 254.1.

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba4e4548993947e6879e90c333d30a97
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

Loading…