Diethyl Ether → HCID 58565364, compound

HRID 2175339Notes

Reaction equation

HRID 2175339 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]=[C:9]2[C:17](N(OC)C)=[O:18])[CH:5]=[CH:6][CH:7]=1.[CH3:23][Mg]Br.CCOCC>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]=[C:9]2[C:17](=[O:18])[CH3:23])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58565343HCID 58565343, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58565364HCID 58565364, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(3-fluorophenyl)-N-methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (0.35 g, 1.2 mmol) in tetrahydrofuran (10 mL) was added 3.0 M methylmagnesium bromide in ether (3.1 mL, 9.4 mmol). The reaction was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl solution and then extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated to give the desired product (0.24 g, 81%). The crude product was used directly in next step. LCMS calculated for C15H12FN2O(M+H)+: m/z=255.1. Found: 255.1.

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5369595a93b4cb79adaa2e56cada47c
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

Loading…