Diethyl Ether → HCID 58565369, compound

HRID 2175351Notes

Reaction equation

HRID 2175351 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[C:19](N(OC)C)=[O:20])#[N:2].[CH3:25][Mg]Br.CCOCC>O1CCCC1>[C:19]([C:4]1[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:6]2[C:11]([C:3]=1[C:1]#[N:2])=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:20])[CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58565345HCID 58565345, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58565369HCID 58565369, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-cyano-1-(3-fluorophenyl)-N-methoxy-N-methyl-1H-indole-2-carboxamide (90 mg, 0.28 mmol) in tetrahydrofuran (3 mL) was added 3.0 M methylmagnesium bromide in ether (0.93 mL, 2.8 mmol). The reaction was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-15% EtOAc/hexane) to give the desired product (43 mg, 56%). LCMS calculated for C17H12FN2O(M+H)+: m/z=279.1. Found: 279.0.

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 0-15% EtOAc/hexane)

Sources & evidence

ORD record
ord-676ad632593e494f9961602bb47841a1
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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