Potassium Carbonate → 4-{3-[2-(Benzhydrylidene-amino)-4-(4-fluoro-phenyl)-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

HRID 2075675Notes

Reaction equation

HRID 2075675 reaction equation
[C:1](=[N:14][C:15]1[CH:24]=[C:23](Cl)[C:22]2[C:17](=[CH:18][C:19]([S:26][C:27]3[CH:28]=[C:29]([C:33]4([C:39]#[N:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:30]=[CH:31][CH:32]=3)=[CH:20][CH:21]=2)[N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:41][C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1](=[N:14][C:15]1[CH:24]=[C:23]([C:45]2[CH:46]=[CH:47][C:42]([F:41])=[CH:43][CH:44]=2)[C:22]2[C:17](=[CH:18][C:19]([S:26][C:27]3[CH:28]=[C:29]([C:33]4([C:39]#[N:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:30]=[CH:31][CH:32]=3)=[CH:20][CH:21]=2)[N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 866138264-{3-[2-(Benzhydrylidene-amino)-4-chloro-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 866138284-{3-[2-(Benzhydrylidene-amino)-4-(4-fluoro-phenyl)-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

3c (400 mg, 0.72 mmol), 4-fluorobenzeneboronic acid (150 mg, 1.07 mmol), potassium carbonate (247 mg, 1.79 mmol), and Pd(PPh3)4 (82 mg, 0.07 mmol) were dissolved in 2:1 DME:H2O (10 mL) at degassed for 5 minutes with N2. The reaction was then sealed and heated to 80° C. overnight. After cooling to room temperature, the reaction was concentrated and purified by silica gel chromatography (10% MeOH in CH2Cl2) to give the desired product, 3d.

Workup

  1. customH2O (10 mL) at degassed for 5 minutes with N2
  2. customThe reaction was then sealed
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction was concentrated
  5. custompurified by silica gel chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f63129d700284a968933d3328c5db0f4
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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