Diisopropylethylamine → 3-(5-Phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-benzoic acid

HRID 2075733Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

8-Iodo-5-phenyl-[1,2,4]triazolo[4,3-a]quinoline (250 mg, 0.67 mmol), 3-mercaptobenzoic acid (120 mg, 0.81 mmol), iPr2NEt (0.36 mL, 2.1 mmol), Pd2dba3 (15 mg, 0.02 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (19 mg, 0.03 mmol) were dissolved in 1,4-dioxane and degassed with N2. The reaction was then sealed and heated to 70° C. for 30 minutes, followed by cooling to room temperature, filtration, and concentration to give the desired product, 11a.

Workup

customdegassed with N2
customThe reaction was then sealed
temperatureby cooling to room temperature
filtrationfiltration, and concentration

Sources & evidence

ORD record: ord-01a686bb7db34a8c8a9e58d60647903b
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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