Diisopropylethylamine → 8-[3-(4-Cyano-tetrahydro-pyran-4-yl)-phenylsulfanyl]-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

HRID 2075667Notes

Reaction equation

HRID 2075667 reaction equation
[CH2:1]([O:3][C:4]([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:5])[CH3:2].[SH:26][C:27]1[CH:28]=[C:29]([C:33]2([C:39]#[N:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:30]=[CH:31][CH:32]=1.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]>[CH2:1]([O:3][C:4]([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]([S:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]5([C:39]#[N:40])[CH2:34][CH2:35][O:36][CH2:37][CH2:38]5)[CH:28]=4)=[CH:13][CH:14]=3)[N:9]2[CH:25]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 670906998-Iodo-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

Product 1

HCID 248758648-[3-(4-Cyano-tetrahydro-pyran-4-yl)-phenylsulfanyl]-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

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

Conditions

Temperature
60 °C

Procedure

1v (262 mg, 0.59 mmol), 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (1w, 130 mg, 0.59 mmol), Pd2dba3 (14 mg, 0.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (17 mg, 0.03 mmol), and iPr2NEt (0.27 mL, 1.9 mmol) were dissolved in 1,4-dioxane (2 mL) and degassed with N2 for 10 minutes. The mixture was heated at 60° C. for 2 hours, then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography to give the desired product, 1z.

Workup

  1. customdegassed with N2 for 10 minutes
  2. temperaturecooled to room temperature
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-91b7fc21fba743de9f3d9aa1dc9bf72c
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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