Diisopropylethylamine → 4-[3-([1,2,4]Triazolo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075709Notes

Reaction equation

HRID 2075709 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[N:12]=[CH:13][N:14]=[C:7]1[CH:6]=[CH:5]2.[SH:15][C:16]1[CH:17]=[C:18]([C:22]2([C:28]#[N:29])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=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]>[N:12]1[N:8]2[C:9]3[C:4]([CH:5]=[CH:6][C:7]2=[N:14][CH:13]=1)=[CH:3][C:2]([S:15][C:16]1[CH:17]=[C:18]([C:22]2([C:28]#[N:29])[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH:19]=[CH:20][CH:21]=1)=[CH:11][CH:10]=3

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 582577957-Bromo-[1,2,4]triazolo[1,5-a]quinoline

Product 1

HCID 670911284-[3-([1,2,4]Triazolo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

8b (66 mg, 0.25 mmol) and 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (8c, 90 mg, 0.32 mmol) were dissolved in 1,4-dioxane (5 mL) and degassed for 10 minutes with N2. iPr2NEt (0.15 mL, 0.80 mmol) was added, followed by Pd2dba3 (10 mg, 0.01 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (12 mg, 0.02 mmol), and the mixture was degassed with N2 for an additional 10 minutes. The reaction was sealed and heated overnight at 110° C. Additional catalyst was added after 24 hours to push the reaction to completion, and the mixture was heated at 110° C. for another 2 hours. The reaction was cooled to room temperature and purified by silica gel chromatography (25-100% EtOAc in hexanes) to give the desired product, 8d.

Workup

  1. customdegassed for 10 minutes with N2
  2. customthe mixture was degassed with N2 for an additional 10 minutes
  3. customThe reaction was sealed
  4. additionAdditional catalyst was added after 24 hours
  5. customthe reaction to completion
  6. temperaturethe mixture was heated at 110° C. for another 2 hours
  7. temperatureThe reaction was cooled to room temperature
  8. custompurified by silica gel chromatography (25-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-45a45d6824b348a1a6ffb48dc908c429
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

Loading…