Diethylamine → 5-bromo-N,N-diethyl-2-(6-fluoropyridin-2-yloxy)benzamide

HRID 335826Notes

Reaction equation

HRID 335826 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:41]([NH:43][CH2:44][CH3:45])[CH3:42]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=2)=[C:6]([CH:10]=1)[C:7]([N:43]([CH2:44][CH3:45])[CH2:41][CH3:42])=[O:9]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 673831645-Bromo-2-(6-fluoropyridin-2-yloxy)benzoic acid

Product 1

HCID 673832225-bromo-N,N-diethyl-2-(6-fluoropyridin-2-yloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To mixture of 5-bromo-2-(6-fluoropyridin-2-yloxy)benzoic acid (16 g, 51.3 mmol) and TBTU (16.46 g, 51.3 mmol) in 15 mL of DMF was added diethylamine (13.26 mL, 128 mmol). The resulting solution was allowed to stir at rt overnight. The reaction was quenched with saturated NaHCO3, extracted with a 2:1 mixture of EtOAc and hexanes (3×50 mL). The combined organics were washed with brine, and evaporated to dryness. Purification by silica gel chromatography (hexane to CH2Cl2 to CH2Cl2/EA=20:1 to 10:1 to 5:1) provided 5-bromo-N,N-diethyl-2-(6-fluoropyridin-2-yloxy)benzamide as a off-white solid.

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with a 2:1 mixture of EtOAc and hexanes (3×50 mL)
  3. washThe combined organics were washed with brine
  4. customevaporated to dryness
  5. customPurification by silica gel chromatography (hexane to CH2Cl2 to CH2Cl2/EA=20:1 to 10:1 to 5:1)

Sources & evidence

ORD record
ord-8af583e6674341ef966bed2c01cacd62
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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