Ammonium Chloride → HCID 21097263, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[Li+].C[Si]([N-:44][Si](C)(C)C)(C)C.[NH4+].[Cl-]>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.C1COCC1>[CH3:11][Si:10]([C:9]#[C:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:44])[CH:7]=1)([CH3:13])[CH3:12]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
2-Chloro-4-trimethylsilanylethynyl-pyridine (9.3 g, 44 mmol), tris(dibenzylideneacetone)dipalladium(0) (8.1 g, 8.9 mmol) and 2-(dicyclohexylphosphino)biphenyl (8.1 g, 23 mmol) are added into the de-gased dry THF (60 mL). Then 1.0 M LiHMDS (155 mL, 155 mmol) is added. The reaction mixture is heated at 60° C. for 16 hrs before it is cooled down to room temperature and saturated NH4Cl aqueous solution (100 mL) is added along with water (100 mL). The mixture is extracted with EtOAc (2×200 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using 33% EtOAc in hexanes affords 7.9 g of the desired product.
Workup
- temperatureis cooled down to room temperature
- extractionThe mixture is extracted with EtOAc (2×200 mL)
- concentrationconcentrated
- customto give the crude product
- customPurification by silica flash column chromatography
Sources & evidence
- ORD record
- ord-12f80713b4914e53bcb3af4174cf1a70
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722709B2
Reaction notes
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