1-[7-Bromo-5-(5-methoxy-pyridin-3-yl)-benzothiazol-2-yl]-3-ethyl-urea → 1-Ethyl-3-[5-(5-methoxy-pyridin-3-yl)-7-pyridin-2-yl-benzothiazol-2-yl]-urea

HRID 447034Notes

Reaction equation

HRID 447034 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]=[C:21]([O:23][CH3:24])[CH:22]=2)[CH:3]=1.[Br-].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Zn+]>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:15]([NH:14][C:12]([NH:11][C:8]1[S:9][C:10]2[C:2]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)=[CH:3][C:4]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([O:23][CH3:24])[CH:22]=3)=[CH:5][C:6]=2[N:7]=1)=[O:13])[CH3:16]

Participants

5

Reactant 2

HCID 578137111-[7-Bromo-5-(5-methoxy-pyridin-3-yl)-benzothiazol-2-yl]-3-ethyl-ureaHCID 178418723HCID 178418723, compound

Product 1

HCID 578135761-Ethyl-3-[5-(5-methoxy-pyridin-3-yl)-7-pyridin-2-yl-benzothiazol-2-yl]-ureaYield 28%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-[7-Bromo-5-(5-methoxy-pyridin-3-yl)-benzothiazol-2-yl]-3-ethyl-urea (90 mg, 0.22 mmol), and bis(triphenylphosphine)palladium(II) chloride (10 mg, 0.015 mmol), in tetrahydrofuran (4 ml), was added 2-pyridylzinc bromide (3.1 ml, 1.5 mmol, 0.5 M solution in THF). The reaction was purged with nitrogen then heated at 60° C. for 16 h. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride solution followed by brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by preparative HPLC to give 1-Ethyl-3-[5-(5-methoxy-pyridin-3-yl)-7-pyridin-2-yl-benzothiazol-2-yl]-urea as a white solid (25 mg, 27%)

Workup

  1. customThe reaction was purged with nitrogen
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed with saturated aqueous ammonium chloride solution
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-7ffeea1f59a443d6b73f999c6e1c16df
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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