4-Iodobenzonitrile → 4-(7-hydroxyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)benzonitrile

HRID 1677656

반응식

HRID 1677656 반응식
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH:15]1[N:19]=[CH:18][N:17]2[CH2:20][CH2:21][C:22](=[O:23])[C:16]=12.Cl.ClCCl>O1CCCC1>[OH:23][C:22]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[C:16]2[N:17]([CH:18]=[N:19][CH:15]=2)[CH2:20][CH2:21]1

참가 물질

6

반응물 4

HCID 764674-IodobenzonitrileHCID 111709605,6-Dihydropyrrolo[1,2-c]imidazol-7-oneHCID 19696284HCID 19696284, 화합물HCID 178418918HCID 178418918, 화합물

생성물 1

HCID 669339384-(7-hydroxyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 8.18 mmol of 4-iodobenzonitrile [3058-39-7] in 20 ml of tetrahydrofuran at −20° C. is admixed dropwise with 8.18 mmol of isopropylmagnesium chloride (2M in tetrahydrofuran) and the reaction mixture is subsequently stirred for 15 minutes. A mixture of 4.09 mmol of 5,6-dihydropyrrolo[1,2-c]imidazol-7-one [426219-43-4] in 5 ml of tetrahydrofuran is added. After 1 hour the reaction mixture is poured into 1:1 1N HCl/dichloromethane and the phases are separated. The aqueous phase is rendered basic with saturated sodium hydrogen carbonate solution, stirred thoroughly, extracted with tert-butyl methyl ether (in order to separate unreacted ketone) and then extracted with dichloromethane (3×). The combined dichloromethane phases are dried with sodium sulphate and evaporated. From the residue the title compound is obtained by means of flash chromatography (SiO2 60F) as a white foam. Rf=0.20 (dichloromethane/ammonia (2M in EtOH) 95:5), Rt=3.81 (Gradient I).

후처리

  1. customat −20° C.
  2. additionis added
  3. customthe phases are separated
  4. stirringstirred thoroughly
  5. extractionextracted with tert-butyl methyl ether (in order to separate unreacted ketone)
  6. extractionextracted with dichloromethane (3×)
  7. dry with materialThe combined dichloromethane phases are dried with sodium sulphate
  8. customevaporated

출처 및 근거

ORD 기록
ord-34196859059641f29903415583a32243
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008334B2

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