Ethyl chloroformate → HCID 57419918、化合物

HRID 420974ノート

反応式

HRID 420974 の反応式
[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]

参加物

7

反応物 5

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 57419917HCID 57419917、化合物HCID 178418918HCID 178418918、化合物

生成物 1

HCID 57419918HCID 57419918、化合物

試薬・触媒・溶媒 1

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-a723b68bf37d49e3ae7a0f5f8691266d
出典データセット
uspto-grants-2012_01
特許番号
US08097623B2

反応ノート

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