5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide → HCID 90093975, compound

HRID 1753048Notes

Reaction equation

HRID 1753048 reaction equation
I[C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=1.[Li]CCCC.[Br:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:31]=1)[C:25](N(OC)C)=[O:26]>C(OCC)C>[Br:19][C:20]1[CH:31]=[C:24]([C:25]([C:2]2[C:6]3[CH:7]=[N:8][CH:9]=[CH:10][C:5]=3[N:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=2)=[O:26])[CH:23]=[N:22][CH:21]=1

Participants

5

Reactant 3

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 90093879HCID 90093879, compoundHCID 178418339Butyllithium

Product 1

HCID 90093975HCID 90093975, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 3-iodo-1-isopropyl-1H-pyrrolo[3,2-c]pyridine (Preparation 45, 13 g, 45.43 mmol) in anhydrous diethyl ether (120 mL) at −78° C. was added nBuLi (28.69 mL, 54.5 mmol) dropwise under nitrogen. After stirring at this temperature for 30 minutes, 5-bromo-N-methoxy-N-methylnicotinamide (11.13 g, 45.43 mmol) in diethylether (10 mL) was added dropwise before warming the reaction to room temperature for 18 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution, extracted into EtOAc, the organic layer collected, dried over Na2SO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 80-90% EtOAc in hexanes to afford the title compound as a yellow solid.

Workup

  1. temperaturebefore warming
  2. customthe reaction to room temperature for 18 hours
  3. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution
  4. extractionextracted into EtOAc
  5. customthe organic layer collected
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified
  9. washeluting with 80-90% EtOAc in hexanes

Sources & evidence

ORD record
ord-2333e517ee2d41da8abf9278376a86e6
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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