Triphenylphosphine → N-(5-bromo-pyridin-2-yl)-2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionamide

HRID 966857Notes

Reaction equation

HRID 966857 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH2:39][CH:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)[C:36]([OH:38])=O)=[CH:31][C:30]=1[N+:45]([O-:47])=[O:46].[NH2:48][C:49]1[CH:54]=[CH:53][C:52]([Br:55])=[CH:51][N:50]=1>C(Cl)Cl>[Br:55][C:52]1[CH:53]=[CH:54][C:49]([NH:48][C:36](=[O:38])[CH:35]([C:32]2[CH:33]=[CH:34][C:29]([Cl:28])=[C:30]([N+:45]([O-:47])=[O:46])[CH:31]=2)[CH2:39][CH:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)=[N:50][CH:51]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 706222-Amino-5-bromopyridineHCID 223152892-(4-Chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid

Product 1

HCID 22315146N-(5-bromo-pyridin-2-yl)-2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionamideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of triphenylphosphine (241 mg, 0.92 mmol) in methylene chloride (3 mL) was cooled to 0° C. and then slowly treated with N-bromosuccinimide (164 mg, 0.92 mmol). The reaction mixture was stirred at 0° C. for 10 min and then treated with 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid (prepared as in Example 64, 250 mg, 0.84 mmol). The resulting reaction mixture was stirred at 0° C. for 5 min and then allowed to warm to 25° C. where it was stirred for 30 min. The reaction mixture was then treated with 2-amino-5-bromopyridine (320 mg, 1.85 mmol). The crude reaction mixture was then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) to afford N-(5-bromo-pyridin-2-yl)-2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionamide (216 mg, 57%) as a pale yellow solid: mp 128-130° C.; EI-HRMS m/e calcd for C19H19BrClN3O3 (M+) 451.0298, found 451.0300.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 0° C. for 5 min
  3. temperatureto warm to 25° C. where it
  4. stirringwas stirred for 30 min
  5. customThe crude reaction mixture
  6. customwas then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-53b8a07cb6624d768b8a1747b81d2d22
Source dataset
uspto-grants-2005_10
Patent number
US06951945B2

Reaction notes

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