Triethylamine → 5-bromo-N-(2-(phenylamino)phenyl)nicotinamide

HRID 520823Notes

Reaction equation

HRID 520823 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:11]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N=C=NC(C)C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12734DiisopropylcarbodiimideHCID 68297N-Phenyl-o-phenylenediamineHCID 887075-Bromonicotinic acid

Product 1

HCID 706542275-bromo-N-(2-(phenylamino)phenyl)nicotinamideYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-bromonicotinic acid (20.0 g, 99 mmol), N-phenyl-o-phenylenediamine (19.32 g, 105 mmol), diisopropylcarbodiimide (DIC) (26.5 g, 210 mmol), and triethylamine (Et3N)(2.65 g, 27 mmol) in DCM (anhydrous, 350 mL) was heated to about 50° C. and degassed overnight under argon. After cooling to RT, the solids were then filtered off. The filtrate was washed with water (2×200 mL), dried over sodium sulfate and loaded onto silica gel. A flash column (gradient of 3% to 10% ethyl acetate in DCM) gave 30.32 g of 1E; 83% yield, pure by HNMR.

Workup

  1. customdegassed overnight under argon
  2. temperatureAfter cooling to RT
  3. filtrationthe solids were then filtered off
  4. washThe filtrate was washed with water (2×200 mL)
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-76a437a440364558827b5be2dee0c581
Source dataset
uspto-grants-2016_05
Patent number
US09328094B2

Reaction notes

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