Triethylamine → HCID 54718752, compound

HRID 1244107Notes

Reaction equation

[OH:1][C:2]1[C:3]2[C:13]([C:14]3[S:15][C:16](I)=[C:17]([CH3:19])[CH:18]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9].CCN(CC)CC.[CH2:28]([O:31][CH3:32])[C:29]#[CH:30]>CN(C=O)C.[Cu]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>[OH:1][C:2]1[C:3]2[C:13]([C:14]3[S:15][C:16]([C:30]#[C:29][CH2:28][O:31][CH3:32])=[C:17]([CH3:19])[CH:18]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9]

Participants

Conditions

Temperature: 60 °C

Procedure

4-hydroxy-3-(5-iodo-4-methylthien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (200 mg, 0.48 mmol, Example 222) was dissolved in DMF (2.4 ml). Et3N 0.133 ml, 0.96 mmol) and methyl propargyl ether (0.202 ml, 2.4 mmol) were added and the mixture was degassed with N2 for 2 min. CuI (9.1 mg, 0.048 mmol) and PdCl2(PPh3)2 (17 mg, 0.024 mmol) were added, the vessel was capped and the reaction was heated at 60° C. with stirring for 2.5 h. The reaction mixture was then cooled and filtered through a plug of silica gel eluting with CH2Cl2→EtOH. The organics were removed by rotary evaporation and the residue was purified by RP-HPLC to give the title compound. MS (ESI) m/z 357.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.49 (s, 1H), 6.92 (s, 1H), 4.38 (s, 3H), 2.23 (s, 3H).

Workup

customthe mixture was degassed with N2 for 2 min
customthe vessel was capped
temperatureThe reaction mixture was then cooled
filtrationfiltered through a plug of silica gel eluting with CH2Cl2→EtOH
customThe organics were removed by rotary evaporation
customthe residue was purified by RP-HPLC

Sources & evidence

ORD record: ord-e77d9ac0d6fb48aaaffdc9e89bf10db4
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119205B2

Reaction notes

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