Diisopropylethylamine → 3-(5-Phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-propionic acid 2-ethyl-hexyl ester

HRID 2075735Notes

Reaction equation

I[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][C:8]3[N:9]2[CH:12]=[N:13][N:14]=3)=[CH:4][CH:3]=1.[CH2:21]([CH:23]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:24][O:25][C:26](=[O:30])[CH2:27][CH2:28][SH:29])[CH3:22].CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.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]>[CH2:21]([CH:23]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:24][O:25][C:26](=[O:30])[CH2:27][CH2:28][S:29][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][C:8]3[N:9]2[CH:12]=[N:13][N:14]=3)=[CH:4][CH:3]=1)[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

8-Iodo-5-phenyl-[1,2,4]triazolo[4,3-a]quinoline (900 mg, 3.0 mmol), 3-mercaptopropionic acid 2-ethylhexyl ester (660 mg, 3.0 mmol), iPr2NEt (1.1 mL, 6.3 mmol), Pd2dba3 (69 mg, 0.05 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (87 mg, 0.15 mmol) were dissolved in 1,4-dioxane (15 mL) and degassed for 10 minutes with N2. The reaction was then sealed and heated to 60° C. for 1.5 hours, followed by cooling to room temperature and concentration. The residue was purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 11c.

Workup

customdegassed for 10 minutes with N2
customThe reaction was then sealed
temperatureby cooling to room temperature
concentrationconcentration
customThe residue was purified by silica gel chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7723f19a8f7e453189116ab182052eed
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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