Ethyl chloroformate → HCID 57419918, compound

HRID 420974Notes

Reaction equation

HRID 420974 reaction equation
[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]

Participants

7

Reactant 5

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 57419917HCID 57419917, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57419918HCID 57419918, compound

Reagents, catalysts & solvents 1

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-a723b68bf37d49e3ae7a0f5f8691266d
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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