Diisopropylethylamine → HCID 58257767, compound

HRID 2075721Notes

Reaction equation

HRID 2075721 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.C(C(CCCC)COC(=O)CC[SH:38])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:12]2[N:8]3[C:9]4[C:4]([CH:5]=[CH:6][C:7]3=[N:14][N:13]=2)=[CH:3][C:2]([SH:38])=[CH:11][CH:10]=4)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 926402-Ethylhexyl 3-mercaptopropionateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 582577587-Iodo-1-phenyl-[1,2,4]triazolo[4,3-a]quinoline

Product 1

HCID 58257767HCID 58257767, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To 7-Iodo-1-phenyl-[1,2,4]triazolo[4,3-a]quinoline (1.5 g, 4.0 mmol) in 1,4-dioxane (15 mL) was added iPr2NEt (1.4 mL, 8.1 mmol), and the reaction was degassed with N2 for 10 minutes. 3-Mercapto-propionic acid 2-ethylhexyl ester (975 mg, 4.5 mmol) was added, followed by Pd2dba3 (93 mg, 0.1 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (117 mg, 0.2 mmol). The reaction was sealed and heated overnight at 80° C., and then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (60-100% EtOAc in hexanes) to give the thiol intermediate as an oil. The oil was dissolved in THF (9 mL) and cooled to −78° C. Sodium tert-butoxide (780 mg, 8.1 mmol) was added, and the reaction was stirred at room temperature overnight. The mixture was diluted with 1N NaOH, and the aqueous layer was washed with Et2O. The aqueous layer was acidified with 1N HCl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the crude material was purified by silica gel chromatography (60-100% EtOAc in hexanes) to give the desired product, 10e.

Workup

  1. customthe reaction was degassed with N2 for 10 minutes
  2. customThe reaction was sealed
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (60-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d38bc725e87d421890a673af404cefa8
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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