HCID 58565354, compound → HCID 58565352, compound

HRID 2175322Notes

Reaction equation

HRID 2175322 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18](N(OC)C)=[O:19])[N:6]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.[CH3:24][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18](=[O:19])[CH3:24])[N:6]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1

Participants

4

Reactant 2

HCID 58565354HCID 58565354, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58565352HCID 58565352, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-chloro-1-(3-fluorophenyl)-N-methoxy-N-methyl-1H-indole-2-carboxamide (0.44 g, 1.3 mmol) in tetrahydrofuran (10 mL) was added 1.4 M methylmagnesium bromide in tetrahydrofuran (4.7 mL, 6.6 mmol) dropwise. The reaction was stirred at room temperature overnight, then quenched with aqueous saturated NH4Cl solution and extracted with EtOAc. The extracts were dried over MgSO4, concentrated and purified on silica gel (eluting with 0-10% EtOAc in hexane) to give the desired product (0.26 g, 68%). LCMS calculated for C16H12ClFNO(M+H)+: m/z=288.1. Found: 288.0.

Workup

  1. customquenched with aqueous saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 0-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-a8fd5d948e3c45f9897351120ed210df
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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