Ethyl chloroformate → HCID 57419918, 화합물

HRID 420974노트

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HRID 420974 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1I)=[CH:12][C:11]([Br:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C([Mg]Cl)(C)C.[Li+].[Cl-].Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36].[NH4+].[Cl-]>CN1C(=O)N(C)CCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:12][C:11]([Br:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

참가 물질

7

반응물 5

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 57419917HCID 57419917, 화합물HCID 178418918HCID 178418918, 화합물

생성물 1

HCID 57419918HCID 57419918, 화합물

시약·촉매·용매 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

실험 절차

5-Bromo-3-iodo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (1.0 g, 1.89 mmol; see step (b) above) in anhydrous DMPU (4 mL) was rapidly added to i-PrMgCl.LiCl (1.0 M in THF, 4.2 mmol, 4.2 mL) at −65° C. After 30 min at −65° C., ethyl chloroformate (720 mL, 7.56 mmol) was added and the mixture was allowed to warm to rt and poured into NH4Cl (aq, sat, 200 mL). The mixture was extracted with EtOAc (3×50 ml-L) and the combined extracts were washed with brine, dried (Na2SO4), concentrated and purified by chromatography to afford the sub-title compound. Yield 650 mg (72%).

후처리

  1. customat −65° C
  2. extractionThe mixture was extracted with EtOAc (3×50 ml-L)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by chromatography

출처 및 근거

ORD 기록
ord-a723b68bf37d49e3ae7a0f5f8691266d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097623B2

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