Ammonium Chloride → HCID 21479421, compound

HRID 741725Notes

Reaction equation

HRID 741725 reaction equation
C[Sn](C)(C)[C:3]1[CH:20]=[CH:19][C:6]2[C:7](=[O:18])[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][O:10][C:5]=2[CH:4]=1.[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28](I)[CH:27]=1.[Cl-].[NH4+]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]([C:26]1[CH:27]=[C:28]([C:3]2[CH:20]=[CH:19][C:6]3[C:7](=[O:18])[C:8]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:9][O:10][C:5]=3[CH:4]=2)[CH:29]=[CH:30][CH:31]=1)([O:24][CH3:23])=[O:33]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 69258Methyl 3-iodobenzoateHCID 21852174HCID 21852174, compound

Product 1

HCID 21479421HCID 21479421, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the compound of step F (7.0 g, 17.5 mmole) in dimethylformamide (DMF) (35 mL) was added Pd(PPh3)2Cl2 (490 mg, 0.7 mmole), 3 crystals of BHT and methyl-3-iodobenzoate (5.0 g, 19.1 mmole). The mixture was stirred at reflux for 1.5 hours, cooled to room temperature and poured into 150 mL of saturated aqueous ammonium chloride solution. The mixture was extracted with 3×150 mL of diethyl ether, and the combined extract was washed with 2×100 mL of water, and then brine. The solution was dried over sodium sulfate, filtered and evaporated in vacuo to afford a yellow oil. Chromatography over silica gel (4:1 hexane:ether elution) afforded 6.51 g of the title compound as a viscous oil.

Workup

  1. temperatureat reflux for 1.5 hours
  2. extractionThe mixture was extracted with 3×150 mL of diethyl ether
  3. extractionthe combined extract
  4. washwas washed with 2×100 mL of water
  5. dry with materialThe solution was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a yellow oil

Sources & evidence

ORD record
ord-5f6f9007361246d8bb2d7bffba8be08d
Source dataset
uspto-grants-1996_09
Patent number
US05552435

Reaction notes

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