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

HRID 2075657
Notes
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Reaction equation

HRID 2075657 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[CH:6]=[CH:5]2.[CH2:15]([CH:17]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:18][O:19][C:20](=[O:24])[CH2:21][CH2:22][SH:23])[CH3:16].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]>[CH2:15]([CH:17]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:18][O:19][C:20](=[O:24])[CH2:21][CH2:22][S:23][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[CH:6]=[CH:5]2)[CH3:16]
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 67091020HCID 67091020, compound

Product 1

HCID 670909063-(Imidazo[1,2-a]quinolin-7-ylsulfanyl)-propionic acid 2-ethyl-hexyl ester

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

1g (120 mg, 0.5 mmol) and 3-mercaptopropionic acid 2-ethylhexyl ester (110 mg, 0.5 mmol) were dissolved in 1,4-dioxane (5 mL) and degassed with N2 for 10 minutes. iPr2NEt (0.15 mL, 0.84 mmol), Pd2dba3 (10 mg, 0.01 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (12 mg, 0.02 mmol) were added, and the mixture was degassed with N2 for an additional 10 minutes. The reaction was heated to 80° C. overnight, then cooled to room temperature, concentrated, and purified by silica gel chromatography to give the desired product, 1i.

Workup

  1. customdegassed with N2 for 10 minutes
  2. customthe mixture was degassed with N2 for an additional 10 minutes
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4ae3f1695da94e3da76e8216f7d2c76b
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