Water → HCID 178472856, compound

HRID 411203Notes

Reaction equation

HRID 411203 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[C:26]([C:27](=[O:36])[C:28](=[N+:34]=[N-:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][C:24]([I:37])=[CH:23][N:22]=1.O>C(OC(C)C)(C)C.C(Cl)(Cl)Cl>[Cl:20][C:21]1[C:26]([C:27](=[O:36])[C:28](=[N:34][NH2:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][C:24]([I:37])=[CH:23][N:22]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 76168297HCID 76168297, compound

Product 1

HCID 178472856HCID 178472856, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7914Diisopropyl EtherSolvent

Procedure

Triphenylphosphine(1.95 g) is added in one portion to a solution of ethyl 3-(2-chloro -5-iodo-3-pyridinyl)-2-diazo-3-oxopropanoate (Preparation 19, 2.57 g) in diisopropyl ether (25 mL) and chloroform (15 mL) at room temperature. The yellow solution is stirred under nitrogen for 18 h. The mixture is then treated with water (0.125 mL), heated to reflux for 2 h, and then stirred overnight at room temperature. The mixture is filtered, and the solids are washed with hexane and dried to give 1.83 g of the title compound. After concentration, the filtrate is purified by flash chromatography on silica gel eluted with 10% ethyl acetate/hexane to provide an additional 0.36 g to yield a combined total of 2.19 g (85%) of the title compound as a pale yellow solid. Physical characteristics: 1H NMR (300 MHz, CDCl3) δ 1.39, 1.63, 4.38, 7.94, 8.63; IR (drift) 3378, 3182, 1675, 1651, 1568, 1564, 1483, 1324, 1303, 1286, 1199, 923, 770, 664, 620 cm−1; MS (ESI+) m/z 382 (M+H)+. Anal. Found: C, 31.78; H, 2.43; N, 10.91; Cl, 9.63.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. stirringstirred overnight at room temperature
  4. filtrationThe mixture is filtered
  5. washthe solids are washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-5c7bb975ce0a43b7a7a2fb9eeca139bf
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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