Diisopropylethylamine → 4-[3-(1-Methyl-5-phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-ol

HRID 2075699Notes

Reaction equation

I[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:7][C:8]3[N:9]2[C:12]([CH3:15])=[N:13][N:14]=3)=[CH:4][CH:3]=1.[SH:22][C:23]1[CH:24]=[C:25]([C:29]2([OH:35])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=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:12]1[N:9]2[C:10]3[C:5]([C:6]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7][C:8]2=[N:14][N:13]=1)=[CH:4][CH:3]=[C:2]([S:22][C:23]1[CH:24]=[C:25]([C:29]2([OH:35])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=1)[CH:11]=3

Participants

Conditions

Temperature: 70 °C

Procedure

5u (100 mg, 0.26 mmol), 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-ol (5v, 65 mg, 0.31 mmol), iPr2NEt (0.1 mL, 0.52 mmol), Pd2dba3 (6 mg, 0.01 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (8 mg, 0.01 mmol) were dissolved in 1,4-dioxane (4 mL) and degassed with N2 for 5 minutes. The mixture was heated to 70° C. until no starting material was seen by tlc analysis. The reaction was cooled to room temperature and concentrated, and the residue was purified by silica gel chromatography to give the desired product, 5y.

Workup

customdegassed with N2 for 5 minutes
temperatureThe reaction was cooled to room temperature
concentrationconcentrated
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-b980fc124e174899a2ce95b3b1158c7a
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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