Carbon Dioxide → HCID 11678238, compound

HRID 420972Notes

Reaction equation

HRID 420972 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)[C:8]2[C:13]([C:14]=1I)=[CH:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C([Mg]Cl)(C)C.[Li+].[Cl-].[C:45](=[O:47])=[O:46]>C1COCC1>[CH3:2][CH2:1][O:3][C:4]([C:6]1[N:7]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)[C:8]2[C:13]([C:14]=1[C:45]([OH:47])=[O:46])=[CH:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)=[CH:10][CH:9]=2)=[O:5]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 433294Lithium ChlorideHCID 66657674HCID 66657674, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 11678238HCID 11678238, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Cyclopentyloxyphenyl)-3-iodo-5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester (310 mg, 0.5 mmol; see step (c) above) in THF (2 mL) was added dropwise to i-PrMgCl.LiCl (1.0 M in THF, 500 μL, 0.5 mmol) at −40° C. After 15 min at −40° C., a stream of dry CO2 was passed through the mixture for 5 min and the mixture was allowed to warm to rt. The mixture was partitioned between EtOAc (10 mL) and NH4Cl (aq, sat). The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with H2O and brine, dried (Na2SO4) concentrated and purified by chromatography, followed by recrystallisation from EtOAc/petroleum ether to give the title compound. Yield 70 mg (26%).

Workup

  1. customat −40° C
  2. customThe mixture was partitioned between EtOAc (10 mL) and NH4Cl (aq, sat)
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic phases were washed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by chromatography
  9. customfollowed by recrystallisation from EtOAc/petroleum ether

Sources & evidence

ORD record
ord-df4589ce54ce433e8e36afd730c9a7f6
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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