Aniline → 5-(phenylamino)-N-(2-(piperidin-1-yl)phenyl)furan-2-carboxamide

HRID 33472

Reaction equation

HRID 33472 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([C:16]2[O:17][C:18](Br)=[CH:19][CH:20]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([C:16]2[O:17][C:18]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:20]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6115AnilineHCID 634876Binap, (A+-)-HCID 8891325-bromo-N-(2-piperidin-1-ylphenyl)furan-2-carboxamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 444445845-(phenylamino)-N-(2-(piperidin-1-yl)phenyl)furan-2-carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-furan-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide (1.0 mmol) in toluene (7.5 mL) was added aniline (1.3 mmol), tris(dibenzylidineacetone)dipalladium(0) (“Pd2dba”) (Aldrich) (0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (“BINAP”) (0.1 mmol), and potassium tert-butoxide (“t-BuOK”) (1.5 mmol), and the resulting mixture was refluxed overnight. The reaction was then cooled to room temperature, passed through a plug of silica and concentrated. Purification of the dark brown residue by HPLC afforded the product. Yield: 40%. MS: 362 (M+1).

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. concentrationconcentrated
  3. customPurification of the dark brown residue by HPLC
  4. customafforded the product

Sources & evidence

ORD record
ord-0255c1b304a74e0d8db0f77ad6126e01
Source dataset
uspto-grants-2008_09
Patent number
US07429603B2

Linked notes

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