Diisopropylethylamine → 4-[3-(2-Methyl-imidazo[1,2-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075660Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[C:13]([CH3:15])[N:14]=[C:7]1[CH:6]=[CH:5]2.[SH:16][C:17]1[CH:18]=[C:19]([C:23]2([C:29]#[N:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1.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]>[CH3:15][C:13]1[N:14]=[C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([S:16][C:17]4[CH:18]=[C:19]([C:23]5([C:29]#[N:30])[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)[CH:20]=[CH:21][CH:22]=4)[CH:3]=3)[N:8]2[CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1m (30 mg, 0.13 mmol) and 4-(3-mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (1n, 35 mg, 0.11 mmol) were dissolved in 1,4-dioxane (4 mL) and degassed with N2 for 10 minutes. iPr2NEt (0.04 mL, 0.22 mmol), Pd2dba3 (catalytic), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (catalytic) 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 preparative HPLC to give the desired product, 1o.

Workup

customdegassed with N2 for 10 minutes
customthe mixture was degassed with N2 for an additional 10 minutes
temperaturecooled to room temperature
concentrationconcentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-c65009b541c24e549299547c84699d85
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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