Diethylamine → 5-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide

HRID 529423Notes

Reaction equation

HRID 529423 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[C:13]([F:18])=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[C:13]([F:18])=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([N:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[O:9]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66728313HCID 66728313, compound

Product 1

HCID 667282945-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of crude 5-bromo-2-(2-fluoropyridin-3-yloxy)benzoic acid (8.00 g, 25.6 mmol), diethylamine (6.63 mL, 64.1 mmol) and TBTU (8.23 g, 25.6 mmol) in 8 mL of DMF was stirred overnight. The reaction was quenched with Sat. NaHCO3, extracted with EA/H=2:1, washed with brine, dried over Na2 SO4, filtered and evaporated to dryness. CC (DCM to DCM/EA 100:5 to 100:10 to 100:20 to 3:1) gave 5-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide as a yellow solid.

Workup

  1. customThe reaction was quenched with Sat. NaHCO3
  2. extractionextracted with EA/H=2:1
  3. washwashed with brine
  4. customdried over Na2 SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-118ff6ec6d1f411f8d56b4b73f4b488b
Source dataset
uspto-grants-2016_05
Patent number
US09346827B2

Reaction notes

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