1,2-Dimethoxyethane → HCID 59299334, compound

HRID 2235321Notes

Reaction equation

HRID 2235321 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][CH:11]=1)=[O:5])C.Br[C:16]1[C:17]([Cl:36])=[C:18]([C:32]([Cl:35])=[CH:33][CH:34]=1)[CH2:19][CH:20]1[CH2:24][CH2:23][N:22]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:21]1=[O:31].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[Cl:35][C:32]1[C:18]([CH2:19][CH:20]2[CH2:24][CH2:23][N:22]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:21]2=[O:31])=[C:17]([Cl:36])[CH:16]=[CH:34][C:33]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 3249312(3-Ethoxycarbonylphenyl)boronic acidHCID 11668579HCID 11668579, compound

Product 1

HCID 59299334HCID 59299334, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Place 3-(ethoxycarbonyl)phenylboronic acid (670 mg, 3.46 mmol), 3-(3-bromo-2,6-dichlorobenzyl)-1-cyclohexylpyrrolidin-2-one (Example 50) (700 mg, 1.73 mmol), and Pd(PPh3)4 (173 mg, 0.173 mmol) into a flask and purge with nitrogen. Add DME (50 mL) and 2M sodium carbonate (5 mL) and heat to 75° C. for 24 hr. Cool reaction, add DCM and wash with saturated sodium bicarbonate. Dry, filter, and concentrate organic layer. Purify by silica gel (30-45% EtOAc in Hex). Dissolve ester in ethanol (3 mL) and water (1 mL) and add KOH (291 mg, 5.18 mmol. Stir for 1 hour at room temperature. Strip off solvent and add water. Bring to a pH of 2 with 1M HCl. Filter precipitate to give 727 mg (94%) of title compound as a white solid. Mass spectrum (apci) m/z=446.2 (M+H).

Workup

  1. temperatureCool
  2. customreaction
  3. washwash with saturated sodium bicarbonate
  4. customDry
  5. filtrationfilter
  6. concentrationconcentrate organic layer
  7. customPurify by silica gel (30-45% EtOAc in Hex)
  8. additionDissolve ester in ethanol (3 mL) and water (1 mL) and add KOH (291 mg, 5.18 mmol
  9. additionStrip off solvent and add water
  10. filtrationFilter precipitate

Sources & evidence

ORD record
ord-074b0eb95f2443679bbe615ca914f1df
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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