N,N-Dimethylaniline → HCID 23110951, compound

HRID 2373686Notes

Reaction equation

HRID 2373686 reaction equation
[NH2:1][C:2]1[C:3]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[N:4][C:5]([CH3:14])=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].CN(C)C1C=CC=CC=1.[Br:29][CH2:30][C:31](Br)=[O:32]>ClCCl>[Br:29][CH2:30][C:31]([NH:1][C:2]1[C:3]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[N:4][C:5]([CH3:14])=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:12])[F:13])=[O:32]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 23110956HCID 23110956, compound

Product 1

HCID 23110951HCID 23110951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Amino-2-[(2-methoxyethyl)oxy]-6-methyl-4-[(2,2,2-trifluoroethyl)oxy]pyridine (1.39 g, 4.96 mmol) was dissolved in dichloromethane (15 mL). N,N-dimethylaniline (0.76 g, 6.27 mmol) was added to the solution. Under stirring on an ice bath, bromoacetyl bromide (1.16 g, 5.75 mmol) in dichloromethane (5 mL) was added dropwise to the mixture, followed by stirring at the same temperature for 30 minutes. The reacion mixture was directly subjected to silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1→n-hexane/acetone=1/1) for purification, to thereby yield 2-bromo-N-[2-[(2-methoxyethyl)oxy]-6-methyl-4-[(2,2,2-trifluoroethyl)oxy]pyridin-3-yl]acetamide as a colorless solid (1.98 g, 99%).

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. customThe reacion mixture was directly subjected to silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1→n-hexane/acetone=1/1) for purification

Sources & evidence

ORD record
ord-bccb4b96be024365b1358318254b7b97
Source dataset
uspto-grants-2008_12
Patent number
US07459552B2

Reaction notes

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