1,4-Dioxane → HCID 59164488, compound

HRID 906620Notes

Reaction equation

HRID 906620 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](I)[C:7]([CH:11]([CH3:13])[CH3:12])=[CH:6][C:5]=1[NH2:14].O1CCO[CH2:18][CH2:17]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:17]#[CH:18])[C:7]([CH:11]([CH3:13])[CH3:12])=[CH:6][C:5]=1[NH2:14]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 29928205Methyl 2-amino-5-iodo-4-(propan-2-yl)benzoate

Product 1

HCID 59164488HCID 59164488, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of 2-amino-5-iodo-4-isopropyl-benzoic acid methyl ester (1.5 g, 4.7 mmol), Bu3SnCCH (1.5 mL, 5.17 mmol) and (Ph3P)4Pd (271.6 mg, 0.235 mmol) in dioxane (80 mL) was heated at 120° C. for 1.5 h. The solvent was removed in vacuo. The residue was purified by two successive flash chromatographies (160 g silica gel, hexanes→EtOAc:hexanes (3:7 to 1:1), then (50 g silica gel, hexanes→EtOAc:hexanes (1:9)) to provide 2-amino-5-ethynyl-4-isopropyl-benzoic acid methyl ester (738 mg, 72%) as a yellowish oil. API-ES: m/z 218 [M+H]+, rt 5.45 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by two successive flash chromatographies (160 g silica gel, hexanes→EtOAc:hexanes (3:7 to 1:1)

Sources & evidence

ORD record
ord-75716369a9c946408fe80ffdeca6bb02
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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