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

HRID 2075668Notes

Reaction equation

C(OC([C:6]1[N:7]=[C:8]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]3[C:10](=[CH:11][C:12](I)=[CH:13][CH:14]=3)[N:9]2[CH:25]=1)=O)C.[CH2:26]([CH:28]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:29][O:30][C:31](=[O:35])[CH2:32][CH2:33][SH:34])[CH3:27].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.CCN(C(C)C)C(C)C>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]>[CH2:26]([CH:28]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:29][O:30][C:31](=[O:35])[CH2:32][CH2:33][S:34][C:12]1[CH:11]=[C:10]2[C:15]([C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:17][C:8]3[N:9]2[CH:25]=[CH:6][N:7]=3)=[CH:14][CH:13]=1)[CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

1v (900 mg, 2.4 mmol), 3-mercaptopropionic acid 2-ethylhexyl ester (660 mg, 3.0 mmol), Pd2dba3 (69 mg, 0.08 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (87 mg, 0.15 mmol), and iPr2NEt (1.1 mL, 6.0 mmol) were dissolved in 1,4-dioxane (15 mL) and degassed with N2 for 10 minutes. The mixture was heated at 60° C. for 1.5 hours, then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the desired product, 1x.

Workup

customdegassed with N2 for 10 minutes
temperaturecooled to room temperature
concentrationconcentrated
customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7da62ddf41b947c4b7557ae7125726fd
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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