4-Chloropyridine → 4-Chloro-3-[4-(4-chlorophenyl)-2-thiazolyl]pyridine

HRID 1830866Notes

Reaction equation

HRID 1830866 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[CH:4][CH:3]=1.ClC1C=CN=CC=1.[Li+].CC([N-]C(C)C)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=C(Br)[S:35][CH:36]=2)=[CH:28][CH:27]=1>[Cl-].[Cl-].[Zn+2].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>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:33]=[C:8]([C:7]3[CH:6]=[N:5][CH:4]=[CH:3][C:2]=3[Cl:1])[S:35][CH:36]=2)=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 122884-ChloropyridineHCID 2724682Lithium diisopropylamideHCID 140466744-Chloropyridine-3-carbaldehydeHCID 220497472-Bromo-4-(4-chlorophenyl)-1,3-thiazole

Product 1

HCID 220496904-Chloro-3-[4-(4-chlorophenyl)-2-thiazolyl]pyridineYield 40%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
-78 °C

Procedure

According to the synthetic example of compound (19), 4-chloropyridine (1.14 g, 10.0 mmol) and LDA (12 mmol) were reacted and ZnCl2 (1.63 g, 12.0 mmol) was added to the obtained the reaction mixture. The mixture was stirred at −78° C. for 10 min. and compound (41) (548 mg, 2.0 mmol) and tetrakistriphenylphosphinepalladium (580 mg, 0.5 mmol) were added. The mixture was stirred at room temperature for 30 hrs. The reaction mixture was partitioned between ethyl acetate and NH4Cl aq., and the ethyl acetate layer was washed once with NH4Cl aq. The extract was dried (MgSO4) and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (250 mg, 40%).

Workup

  1. customwere reacted
  2. customobtained the reaction mixture
  3. stirringThe mixture was stirred at room temperature for 30 hrs
  4. customThe reaction mixture was partitioned between ethyl acetate and NH4Cl aq.
  5. washthe ethyl acetate layer was washed once with NH4Cl aq. The extract
  6. dry with materialwas dried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9fb3ddad31e4e55adfdcfc23b698e7c
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

Loading…