1-Methylimidazole → HCID 66707196, compound

HRID 2041444Notes

Reaction equation

HRID 2041444 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-1eb6acb2c9b74eb69e00c3befbf05f14
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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