Iodoethane → HCID 67152582, compound

HRID 602539Notes

Reaction equation

HRID 602539 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][N:12]=[C:13]([C:16]3[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:24][CH3:25])[CH:14]=2)[N:9]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH:8]=1)[CH3:2].[Li+].[CH3:37][CH:38]([N-]C(C)C)C.[CH2:44]1COC[CH2:45]1.C(C1C=CC=CC=1)C.ICC.[NH4+].[Cl-]>C1COCC1>[CH2:1]([O:3][C:4](=[O:35])[C:5]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][N:12]=[C:13]([C:16]3[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:24][CH3:25])[CH:14]=2)[N:9]([C:26]2[CH:27]=[CH:28][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:31]=2)[CH:8]=1)([CH2:44][CH3:45])[CH2:37][CH3:38])[CH3:2]

Participants

7

Reactant 5

HCID 6340IodoethaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 67152479HCID 67152479, compoundHCID 68569164HCID 68569164, compound

Product 1

HCID 67152582HCID 67152582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-propionic acid ethyl ester (120 mg, 0.25 mmol) in THF (3 mL) at −78° C. is added LDA (1.8 M solution in heptate/THF/ethylbenzene, 0.341 mL, 0.61 mmol). The mixture is stirred at −78° C. for 25 minutes and iodoethane (0.20 mL, 2.5 mmol) is added. The mixture is allowed to warm up to room temperature and stirred for 18 hours. To the mixture, an aqueous saturated NH4Cl solution (5 mL) is added, and THF is removed under reduced pressure. The product is extracted with EtOAc. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated under educed pressure. Chromatography of the residue on silica gel (Hexane/EtOAc, 4:1) gives 2-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-2-ethyl-butyric acid ethyl ester as a colorless oil.

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirred for 18 hours
  3. customTHF is removed under reduced pressure
  4. extractionThe product is extracted with EtOAc
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under educed pressure

Sources & evidence

ORD record
ord-134c37da13824bd7bd44c9571e9e66fb
Source dataset
uspto-grants-2011_03
Patent number
US07906528B2

Reaction notes

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