Trifluoroacetic acid → 4-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-ylamine

HRID 1023437Notes

Reaction equation

HRID 1023437 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][C:15](O)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH:11]=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:23]1([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:14][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[CH:13]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 69675871[4-(2-Hydroxy-2-phenyl-2-o-tolyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 690856204-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-ylamineYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

[4-(2-Hydroxy-2-phenyl-2-o-tolyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (361 mg, 0.89 mmol) is dissolved in DCM (4 mL) and trifluoroacetic acid (2.0 mL) is added. After the mixture is stirred for 16 hrs, EtOAc (55 mL) is added followed by the addition of saturated NaHCO3 aqueous solution (15 mL) and water (35 mL). The mixture is stirred for another 15 min and the aqueous layer is separated. The aqueous layer is then extracted with EtOAc (2×35 mL) and all the organic layers are combined and concentrated to give 251 mg of the crude product which is used in the next step without purification.

Workup

  1. stirringThe mixture is stirred for another 15 min
  2. customthe aqueous layer is separated
  3. extractionThe aqueous layer is then extracted with EtOAc (2×35 mL) and all the organic layers
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09215c7abcba4a68b1ca09ba64fd2bf1
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

Loading…