Pyridine → HCID 10804547, compound

HRID 431288Notes

Reaction equation

HRID 431288 reaction equation
N1C=CC=CC=1.[N+:7]([C:10]1[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=1[CH2:12][O:13][C:14]1[C:21]([CH3:22])=[CH:20][C:17]([CH2:18]O)=[CH:16][C:15]=1[CH3:23])([O-:9])=[O:8].[Cl:28]C(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[N+:7]([C:10]1[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=1[CH2:12][O:13][C:14]1[C:21]([CH3:22])=[CH:20][C:17]([CH2:18][Cl:28])=[CH:16][C:15]=1[CH3:23])([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 10565203HCID 10565203, compound

Product 1

HCID 10804547HCID 10804547, compoundYield 165.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (79 mL, 0.97 mmol) was added to a stirring mixture of 8b (112 mg, 0.39 mmol) and triphosgene (46 mg, 0.16 mmol) in CH2Cl2 (5 mL) at r.t. After 15 minutes, the reaction mixture was concentrated in vacuo. Flash chromatography (20 g, 5:1 hexanes/ethyl acetate) yielded 9b (81 mg, 68%) as a white solid: 1H NMR (270 MHz, CDCI3) d 2.27 (s, 6H), 4.52 (s, 2H), 5.23(s, 2H), 7.09 (s, 2H), 7.51 (t, J=8.2 Hz, 1H), 7.76 (t, J=7.4 Hz, 1H), 8.17 (d, J=8.2 Hz, 1H), 8.18 (d, J=7.4 Hz, 1H); 13C NMR (68 MHz, CDCI3) d 16.4, 46.2, 70.1, 124.9, 128.2, 128.4, 129.5, 131.5, 133.5, 134.2, 134.7, 146.6, 155.6.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7e0c37ee3db74feda47883a51d77462a
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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