Diisopropylethylamine → N-(3-Bromo-2-methylphenyl)-3-methoxy-2-pyridineacetamide

HRID 523257Notes

Reaction equation

HRID 523257 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:9][C:10]([O-:12])=O)=[N:5][CH:6]=[CH:7][CH:8]=1.[Na+].[Br:14][C:15]1[C:16]([CH3:22])=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Br:14][C:15]1[C:16]([CH3:22])=[C:17]([NH:18][C:10](=[O:12])[CH2:9][C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1235383-Bromo-o-toluidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117761184Sodium 2-(3-methoxypyridin-2-yl)acetate

Product 1

HCID 117771675N-(3-Bromo-2-methylphenyl)-3-methoxy-2-pyridineacetamideYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of sodium 2-(3-methoxypyridin-2-yl)acetate (0.166 g, 0.871 mmol), 3-bromo-2-methylaniline (0.118 mL, 0.958 mmol), DIEA (0.608 mL, 3.48 mmol) and HATU (0.397 g, 1.05 mmol) in DMF (4.0 mL) was stirred at room temperature. After 1 h, the mixture was diluted with EtOAc and washed twice with 10% aqueous LiCl, then with brine, dried and concentrated. The residue was purified by column chromatography on silica gel to provide N-(3-bromo-2-methylphenyl)-2-(3-methoxypyridin-2-yl)acetamide as a pale yellow solid (0.213 g, 73% yield). Mass spectrum m/z 335, 337 (M+H)+.

Workup

  1. washwashed twice with 10% aqueous LiCl
  2. dry with materialwith brine, dried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4b48eeb9d81146cab8177ef971352f16
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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