Dimethylformamide → HCID 86686878, compound

HRID 533110Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][C:16]2[CH:21]=[C:20]([Br:22])[CH:19]=[CH:18][C:17]=2[OH:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O>[Cu](I)I.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(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[O:23][C:17]3[CH:18]=[CH:19][C:20]([Br:22])=[CH:21][C:16]=3[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 4-(5-bromo-2-hydroxy-phenylethynyl)-piperidine-1-carboxylic acid tert-butyl ester (70 mg), copper iodide (9 mg), N,N-dimethylformamide (1 mL), triethylamine (100 μL), and Pd(PPh3)2Cl2 (7 mg) is heated under an argon atmosphere to 55° C. for 0.5 h. The reaction mixture is diluted with ice water after cooling to room temperature and extracted with ethyl acetate. The combined extracts are dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50) to give the title compound. LC (method 2): tR=1.49 min; Mass spectrum (ESI+): m/z=380, 382 [M+H]+.

Workup

temperatureafter cooling to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined extracts are dried over MgSO4
concentrationconcentrated in vacuo
customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50)

Sources & evidence

ORD record: ord-06141d448c0446f8be625e6d0f70c464
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853239B2

Reaction notes

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