Ammonium Chloride → HCID 69083084, compound

HRID 1023441Notes

Reaction equation

HRID 1023441 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH:5]=[CH:4][N:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[Li+].C[Si]([N-:50][Si](C)(C)C)(C)C.[NH4+].[Cl-]>C1COCC1.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].O>[F:17][C:16]([F:19])([F:18])[C:12]1[CH:11]=[C:10]([CH:9]=[CH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:50])[CH:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 86673607HCID 86673607, compound

Product 1

HCID 69083084HCID 69083084, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-4-[2-(3-trifluoromethyl-phenyl)-vinyl]-pyridine (289 mg, 0.88 mmol), tris(dibenzylideneacetone)dipalladium(0) (160 mg, 0.18 mmol) and 2-(dicyclohexylphosphino)biphenyl (160 mg, 0.46 mmol) are mixed in dry THF (6 mL). Then Argon is bubbled through the solution for 5 min and 1.0 M LiHMDS (3.1 mL, 3.1 mmol) is added. Then the reaction mixture is heated at 65° C. for 16 hrs before the saturated NH4Cl aqueous solution (20 mL) is added along with water (30 mL). The mixture is extracted with EtOAc (3×35 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 193 mg of the desired product.

Workup

  1. customThen Argon is bubbled through the solution for 5 min
  2. extractionThe mixture is extracted with EtOAc (3×35 mL)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-5caeea1c6eac4029b2435307ecea7610
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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