Nitrogen → 4-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

HRID 2075669Notes

Reaction equation

HRID 2075669 reaction equation
C(C(CCCC)COC(=O)C[CH2:8][S:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][C:16]3[N:17]2[CH:20]=[CH:21][N:22]=3)=[CH:12][CH:11]=1)C.N#N.CC(C)([O-])C.[K+].[CH3:42][O:43][C:44]([C:46]1([C:52]2[CH:57]=C[CH:55]=[C:54](Br)[CH:53]=2)[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1)=[O:45].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.CCN(C(C)C)C(C)C>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]>[CH3:42][O:43][C:44]([C:46]1([C:52]2[CH:53]=[CH:54][CH:55]=[C:8]([S:9][C:10]3[CH:19]=[C:18]4[C:13]([C:14]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[CH:15][C:16]5[N:17]4[CH:20]=[CH:21][N:22]=5)=[CH:12][CH:11]=3)[CH:57]=2)[CH2:47][CH2:48][O:49][CH2:50][CH2:51]1)=[O:45]

Participants

9

Reactant 6

HCID 947Nitrogen2×HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23665647Potassium tert-butoxideHCID 670909993-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-propionic acid 2-ethyl-hexyl esterHCID 67091038Methyl 4-(3-bromophenyl)tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 248758664-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

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

Conditions

Temperature
0 °C

Procedure

1x (200 mg, 0.43 mmol) in 1,4-dioxane (5 mL) was degassed with N2 for 10 minutes and cooled to 0° C. Potassium tert-butoxide (73 mg, 0.65 mmol) was added, and the mixture was stirred at room temperature for 5 minutes. The solution was degassed with N2 for another 5 minutes while 4-(3-bromo-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (1y, 130 mg, 0.43 mmol), Pd2dba3 (10 mg, 0.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (11 mg, 0.02 mmol), and iPr2NEt (0.15 mL, 0.87 mmol) were added. The reaction was heated to 60° C. overnight, and then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the desired product, 1z.

Workup

  1. additionwere added
  2. temperatureThe reaction was heated to 60° C. overnight
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4468fc6ac7294dda8247df2651c363dc
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

Loading…