Dimethylamine → HCID 58476637, compound

HRID 1892221Notes

Reaction equation

HRID 1892221 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]/[C:12]([OH:14])=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:15][NH:16][CH3:17].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]/[C:12]([N:16]([CH3:17])[CH3:15])=[O:14])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42553143HCID 42553143, compound

Product 1

HCID 58476637HCID 58476637, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2E)-3-(5-bromo-2-methoxypyridin-3-yl)acrylic acid (1.00 g, 3.87 mmol) in DCM (10 mL) were added dimethylamine (2.0 M in THF, 5.80 mmol), DIEA (2.02 mL, 11.6 mmol) and TBTU (1.49 g, 4.65 mmol). The reaction mixture was allowed to stir at rt overnight. The reaction was quenched with water and then the aqueous solution was extracted with DCM. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give (2E)-3-(5-bromo-2-methoxypyridin-3-yl)-N,N-dimethylacrylamide (1.05 g, 95%) as a white solid. LCMS (FA): Rt=1.68 min, m/z=285.1 (M+H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous solution was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-abb3c9a5fc8d4b4a97e69c7a2288c338
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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