Water → HCID 9881809, compound

HRID 1699736Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6](I)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].O.C[N:22]([CH:24]=O)C>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:24]#[N:22])[CH:5]=2)[CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

3.08 g of the 5-hydroxymethyl-3-iodobenzoic acid methyl ester obtained in the production example 2 was dissolved in 50 ml of dry DMF under the flow of nitrogen and then mixed with 2.32 g of the compound in the production example 3, 2.18 g of potassium carbonate and 456 mg of tetrakis(triphenylphosphine) palladium (0). The obtained mixture solution was heated and stirred at 90° C. overnight, mixed with water to stop the reaction, and then extracted with ethyl acetate. The obtained ethyl acetate layer was dried over MgSO4, and the solvent was distilled away. The residue was purified by silica gel column chromatography to obtain 2.05 g (73%) of the title compound. Colorless crystals.

Workup

temperatureThe obtained mixture solution was heated
customthe reaction
extractionextracted with ethyl acetate
dry with materialThe obtained ethyl acetate layer was dried over MgSO4
distillationthe solvent was distilled away
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2efc357a0fe549d78116f10d9575542f
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348478B1

Reaction notes

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