Acrylic Acid → HCID 67499725, compound

HRID 2402410Notes

Reaction equation

[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC.[C:47]([OH:51])(=[O:50])[CH:48]=[CH2:49]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:49]=[CH:48][C:47]([OH:51])=[O:50])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 28 (500 mg, 1.39 mmol), in DMF (10 mL) at room temperature were added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; 38 mg, 1.67 mmol), tri-o-tolylphosphine (P(o-tol)3, 25 mg, 0.83 mmol), Et3N (483 μμL, 3.48 mmol) and finally acrylic acid (84 μμL, 1.67 mmol). The resulting solution was degassed and purged several times with N2 then heated overnight at 100° C. The solution was filtrated through a Celite pad with a fritted glass funnel then the filtrate was evaporated. The residue was purified by flash chromatography using CH2Cl2/MeOH (95:5) as solvent mixture yielding the title compound 35 (415 mg, 99%) as yellowish solid.

Workup

customThe resulting solution was degassed
custompurged several times with N2
filtrationThe solution was filtrated through a Celite pad with a fritted glass funnel
customthe filtrate was evaporated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-db9496560e0145a5aac0dd162ed62e57
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796330B2

Reaction notes

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