Cesium fluoride → HCID 68934133, compound

HRID 576294Notes

Reaction equation

HRID 576294 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:8]([C:20]#[N:21])=[C:7]2[CH2:22][CH2:23][CH2:24][O:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.[C:36]1([CH3:45])[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1B(O)O.[F-].[Cs+]>COCCOC.CO.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>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH3:45])[C:7]([CH2:22][CH2:23][CH2:24][O:25][C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:29]=[CH:28][CH:27]=3)=[C:8]2[C:20]#[N:21])=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27332672-Methylphenyl boronic acidHCID 68943136HCID 68943136, compound

Product 1

HCID 68934133HCID 68934133, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of EXAMPLE 581C (300 mg) and o-tolylboronic acid (93 mg) in 1,2-dimethoxyethane (10 ml) and methanol (5 ml) was added tetrakis(triphenylphosphine)palladium(0) (33 mg) and CsF (260 mg). The mixture was stirred at reflux under nitrogen for 4 hours. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (300 mL) and water (100 ml). The aqueous layer was further extracted with ethyl acetate and the combined extracts were washed with water, brine and dried over Na2SO4. After filtration, concentration of the solvent and column purification (5 to 10% ethyl acetate in hexane) gave EXAMPLE 581D.

Workup

  1. temperatureat reflux under nitrogen for 4 hours
  2. concentrationThe mixture was concentrated under vacuum
  3. customthe residue was partitioned between ethyl acetate (300 mL) and water (100 ml)
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. washthe combined extracts were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration, concentration of the solvent and column purification (5 to 10% ethyl acetate in hexane)
  8. customgave EXAMPLE 581D

Sources & evidence

ORD record
ord-44580dc19ae449fb93be69a9fc7f376f
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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