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

HRID 2075668
Notes
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Reaction equation

HRID 2075668 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 926402-Ethylhexyl 3-mercaptopropionateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 670906998-Iodo-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

Product 1

HCID 670909993-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-propionic acid 2-ethyl-hexyl ester

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

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

  1. customdegassed with N2 for 10 minutes
  2. temperaturecooled to room temperature
  3. concentrationconcentrated
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes