1-Methylimidazole → HCID 66707196, 화합물

HRID 911577노트

반응식

HRID 911577 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 66707196HCID 66707196, 화합물수율 42%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-7dbc2797f8ca413dace4ee58e959196c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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