Ammonium Chloride → HCID 69081523, compound

HRID 1023444Notes

Reaction equation

HRID 1023444 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([OH:18])([CH3:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:5]=[CH:4][N:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[Li+].C[Si]([N-:49][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>[NH2:49][C:2]1[CH:7]=[C:6]([C:8]([OH:18])([CH3:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 86673608HCID 86673608, compound

Product 1

HCID 69081523HCID 69081523, compoundYield 28.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Chloro-pyridin-4-yl)-1-o-tolyl-propan-2-ol (141 mg, 0.54 mmol), tris(dibenzylideneacetone)dipalladium(0) (99 mg, 0.11 mmol) and 2-(dicyclohexylphosphino)biphenyl (99 mg, 0.28 mmol) are mixed in dry THF (5 mL). Then Argon is bubbled through the solution for 5 min and 1.0 M LiHMDS (2.2 mL, 2.2 mmol) is added. Then the reaction mixture is heated at 65° C. for 16 hrs before the saturated NH4Cl aqueous solution (10 mL) is added along with water (20 mL). The mixture is extracted with EtOAc (3×25 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 37 mg of the desired product.

Workup

  1. customThen Argon is bubbled through the solution for 5 min
  2. extractionThe mixture is extracted with EtOAc (3×25 mL)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-9e151a4289a2466db949b733a3c1b87b
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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