1-Methylimidazole → HCID 66707196, compound

HRID 911577Notes

Reaction equation

HRID 911577 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1.[Br-].[CH3:14][CH:15]([CH3:18])[CH2:16][Zn+].CN1C=CN=C1.ClCCl>CN1CCCC1=O>[CH2:14]([C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1)[CH:15]([CH3:18])[CH3:16]

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 6344DichloromethaneHCID 667070472-bromobenzo[d]thiazole-5-carbonitrileHCID 178448254HCID 178448254, compound

Product 1

HCID 66707196HCID 66707196, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat 2-bromo-benzothiazole-5-carbonitrile (0.3 g, 1.26 mmol) in 1-methyl-pyrrolidinone (4.2 mL) with 2-methylpropylzinc bromide (5 mL, 2.5 mmol, 0.5M solution in THF), N-methylimidazole (0.15 g, 1.88 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (20.5 mg, 0.025 mmol) at 80° C. for 3 h. Cool the mixture and partition between diethyl ether and brine. Dry the organic layer over Na2SO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 1:1 gradient) to give the desired intermediate (113 mg, 42%). MS (EI) m/z: 216 (M+).

Workup

  1. temperatureCool the mixture
  2. custompartition between diethyl ether and brine
  3. dry with materialDry the organic layer over Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 1:1 gradient)

Sources & evidence

ORD record
ord-7dbc2797f8ca413dace4ee58e959196c
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…