Cyanoacetic acid → HCID 10728720, compound

HRID 2207345Notes

Reaction equation

HRID 2207345 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[Br:37][C:38]1[CH:39]=[CH:40][C:41](F)=[N:42][CH:43]=1.[C:45]([CH2:47][C:48]([OH:50])=O)#[N:46]>CN(C=O)C.C(OCC)(=O)C>[Br:37][C:38]1[CH:39]=[CH:40][C:41]([NH:8][C:48](=[O:50])[CH2:47][C:45]#[N:46])=[N:42][CH:43]=1

Participants

7

Reactant 4

HCID 9740Cyanoacetic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 10728720HCID 10728720, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

BOP (3.07 g, 6.94 mmol) and DIEA (606 μl, 3.47 mmol) were added to a mixture of 5-bromo-2-fluoropyridine (400 mg, 2.312 mmol) and cyanoacetic acid (201 mg, 2.358 mmol) in DMF (11.6 mL). The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate and washed with water (2×). The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (ethyl Acetate/hexanes) to afford N-(5-bromopyridin-2-yl)-2-cyanoacetamide. MS ESI calc'd for C8H7BrN3O [M+H]+ 240 and 242. found 240.

Workup

  1. washwashed with water (2×)
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (ethyl Acetate/hexanes)

Sources & evidence

ORD record
ord-f6b4edeb37c7479d90f280394c1dccbc
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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