Diazomethane → HCID 14621982, compound

HRID 1534783Notes

Reaction equation

HRID 1534783 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH:20]([CH3:22])[CH3:21])[C:9]=2[C:23]#[C:24][C:25]([OH:27])=[O:26])=[CH:4][CH:3]=1.[N+](=[CH2:30])=[N-]>C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH:20]([CH3:22])[CH3:21])[C:9]=2[C:23]#[C:24][C:25]([O:27][CH3:30])=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 14621981HCID 14621981, compound

Product 1

HCID 14621982HCID 14621982, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

11.0 g of the crude 3-(4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridin-3-yl)prop-2-ynoic acid were dissolved in 400 ml of diethyl ether, and ethereal diazomethane solution was added in portions until the reaction was complete according to TLC. The solvent was evaporated off and then the remaining crude ester was purified by column chromatography (silica gel; cyclohexane/dichloromethane 1:1). The title compound was obtained in a yield of 8.85 g, corresponding to 98% based on the dibromide employed.

Workup

  1. customThe solvent was evaporated off
  2. customthe remaining crude ester was purified by column chromatography (silica gel; cyclohexane/dichloromethane 1:1)

Sources & evidence

ORD record
ord-1d6fcab767af4871b2836e5b33ae2472
Source dataset
uspto-grants-1992_02
Patent number
US05091386

Reaction notes

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