Diisopropylethylamine → Dicyclopropyl-[3-(1-phenyl-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl)-phenyl]-methanol

HRID 2075726Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][N:14]=[C:7]1[CH:6]=[CH:5]2.CCN(C(C)C)C(C)C.[CH:30]1([C:33]([CH:42]2[CH2:44][CH2:43]2)([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([SH:41])[CH:36]=2)[OH:34])[CH2:32][CH2:31]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>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]>[CH:42]1([C:33]([CH:30]2[CH2:31][CH2:32]2)([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([S:41][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]3[C:12]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)=[N:13][N:14]=[C:7]3[CH:6]=[CH:5]4)[CH:36]=2)[OH:34])[CH2:44][CH2:43]1

Participants

Conditions

Temperature: 100 °C

Procedure

To 7-iodo-1-phenyl-[1,2,4]triazolo[4,3-a]quinoline (10j, 176 mg, 0.47 μmmol) in 1,4-dioxane (4.5 mL) was added iPr2NEt (0.16 mL, 0.94 mmol), and the reaction was degassed with N2 for 5 minutes. 10i (174 mg, 0.47 mmol) was added, followed by Pd2dba3 (22 mg, 0.02 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (28 mg, 0.05 mmol). The reaction was sealed and heated at 100° C. for 6 hours, and then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (60-80% EtOAc in hexanes) to give the desired product, 10k.

Workup

customthe reaction was degassed with N2 for 5 minutes
customThe reaction was sealed
temperaturecooled to room temperature
concentrationconcentrated
customThe residue was purified by silica gel chromatography (60-80% EtOAc in hexanes)

Sources & evidence

ORD record: ord-152f41d5d850493b909391fd84fdb509
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

Loading…