Dimethylamine → HCID 58476637, compound

HRID 2388022Notes

Reaction equation

HRID 2388022 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-4b867f1cb99d41248d42df66d20a74ba
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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