Dichloromethane → 1-Ethyl-3-[7-(5-methyl-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea

HRID 1941970Notes

Reaction equation

HRID 1941970 reaction equation
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].ClCCl.[Br-].[CH3:33][C:34]1[CH:35]=[CH:36][C:37]([Zn+])=[N:38][CH:39]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:15]([NH:14][C:12]([NH:11][C:8]1[S:9][C:10]2[C:2]([C:37]3[CH:36]=[CH:35][C:34]([CH3:33])=[CH:39][N:38]=3)=[CH:3][C:4]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:5][C:6]=2[N:7]=1)=[O:13])[CH3:16]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 248642171-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-ureaHCID 178427808HCID 178427808, compound

Product 1

HCID 578135611-Ethyl-3-[7-(5-methyl-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-ureaYield 4.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(7-bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea (0.25 g, 0.66 mmol) in anhydrous DMF (5.0 mL) was added K2CO3 (0.28 g, 1.99 mmol) and the resulting solution was purged with nitrogen for 15 min. [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (0.054 g, 0.066 mmol) was added to the reaction mixture, purged again with nitrogen for another 15 min followed by addition of 5-methyl-2-pyridyl zinc bromide (3.32 mL, 1.66 mmol). The resulting reaction mixture was stirred at 100° C. for 15 h followed by removal of DMF in vacuo. Water was added and extracted with EtOAc (3×20 mL). The combined organics was washed with brine, dried (Na2SO4) and concentrated. The residue was purified through prep-HPLC to get the desired product (0.011 g, 4%) as an off-white solid.

Workup

  1. additionwas added to the reaction mixture
  2. custompurged again with nitrogen for another 15 min
  3. customThe resulting reaction mixture
  4. customfollowed by removal of DMF in vacuo
  5. additionWater was added
  6. extractionextracted with EtOAc (3×20 mL)
  7. washThe combined organics was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified through prep-HPLC

Sources & evidence

ORD record
ord-583a9ef519a64cbe907614eff0cbf87c
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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