Sodium hydride → HCID 59410096, compound

HRID 1915501Notes

Reaction equation

HRID 1915501 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])([O-:3])=[O:2].[H-].[Na+].[CH3:19][O:20][CH2:21][CH2:22]Br>CN(C=O)C.C(OCC)(=O)C>[CH3:19][O:20][CH2:21][CH2:22][N:10]1[C:11]2[C:7](=[CH:6][C:5]([C:13]([F:16])([F:14])[F:15])=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 593172256-Nitro-5-(trifluoromethyl)-1H-indole

Product 1

HCID 59410096HCID 59410096, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

6-nitro-5-(trifluoromethyl)-1H-indole (50 mg, 0.22 mmol) was dissolved in DMF (2 mL) and treated with sodium hydride (35 mg, 0.87 mmol) to form a dark red opaque solution. The solution was stirred for 20 minutes and then added dropwise to a solution of 2-bromoethyl methyl ether (121 mg, 82 μL, 0.87 mmol) in 1 mL DMF. The reaction mixture was heated at 50° C. for 30 minutes. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with 50% saturated NaHCO3 (2×10 mL) and brine. The organic layer was dried over Na2SO4, filtered and dried to obtain 1-(2-methoxyethyl)-6-nitro-5-(trifluoromethyl)-1H-indole, which was used in the next step without further purification.

Workup

  1. customto form a dark red opaque solution
  2. washwashed with 50% saturated NaHCO3 (2×10 mL) and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-d177d6eb37a141dba25c59400f3e227e
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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