Sodium Carbonate → HCID 57658001, compound

HRID 1670838Notes

Reaction equation

HRID 1670838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20].[CH3:30][O:31][C:32]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)=[O:33].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C(OCC)(=O)C.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>[CH3:30][O:31][C:32]([C:34]1[CH:39]=[CH:38][C:37]([C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([CH2:8][N:9]3[CH2:13][CH2:12][CH:11]([CH:14]4[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)[C:10]3=[O:20])=[C:6]([Cl:21])[CH:5]=2)=[CH:36][CH:35]=1)=[O:33]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 86629496HCID 86629496, compound

Product 1

HCID 57658001HCID 57658001, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Bring a mixture of trifluoro-methanesulfonic acid 3,5-dichloro-4-(3-cyclohexyl-2-oxo-pyrrolidin-1-ylmethyl)-phenyl ester (0.80 g, 1.69 mmol), 4-methoxycarbonylphenylboronic acid (0.457 g, 2.53 mmol), sodium carbonate (0.538 g, 5.07 mmol) in THF (20 mL) and water (5 mL) to 60° C. To the mixture at 60° C., add Pd(PPh3)4 (0.098 g, 0.084 mmol), raise the reaction temperature to 80° C., and stir for 3 hours. Cool the reaction, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify on silica gel column with 20% ethyl acetate in hexanes to afford 0.62 g (80%) of the titled product. MS (m/z): 460 (M+).

Workup

  1. temperatureCool
  2. customthe reaction
  3. washwash with water and brine
  4. dry with materialDry the organic layer (Na2SO4)
  5. customremove the solvent in vacuo
  6. customto afford crude product
  7. custompurify on silica gel column with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3c58270266ad4733a7351ecd3f485ebc
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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