Diisopropylethylamine → 3-(1-Pyridin-2-yl-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl)-propionic acid 2-ethyl-hexyl ester

HRID 2075693Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:13][N:14]=[C:7]1[CH:6]=[CH:5]2.[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:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:13][N:14]=[C:7]1[CH:6]=[CH:5]2)[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

5k (890 mg, 2.4 mmol) and 3-mercaptopropionic acid 2-ethylhexyl ester (630 mg, 2.9 mmol) were dissolved in 1,4-dioxane (20 mL) and degassed with N2 for 10 minutes. iPr2NEt (0.86 mL, 4.8 mmol), Pd2dba3 (54 mg, 0.06 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (69 mg, 0.12 mmol) were added, and the mixture was degassed with N2 for an additional 10 minutes. The reaction was heated to 90° C. until no starting material was seen by tlc analysis, and then the mixture was concentrated and purified by silica gel chromatography to give the desired product, 5m.

Workup

customdegassed with N2 for 10 minutes
customthe mixture was degassed with N2 for an additional 10 minutes
concentrationthe mixture was concentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-9331176e64374c30a437d7b7ffd69f32
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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