Sodium Carbonate → HCID 57658004, compound

HRID 1670847Notes

Reaction equation

HRID 1670847 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]2)[C:10]1=[O:22].[C:32]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.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>[Cl:1][C:2]1[CH:3]=[C:4]([C:44]2[CH:45]=[CH:46][C:41]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:42][CH:43]=2)[CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]2)[C:10]1=[O:22]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 86629498HCID 86629498, compound

Product 1

HCID 57658004HCID 57658004, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Purge with N2 a mixture of trifluoro-methanesulfonic acid 3,5-dichloro-4-[3-(4,4-difluoro-piperidin-1-yl)-2-oxo-pyrrolidin-1-ylmethyl]-phenyl ester (0.097 g, 0.19 mmol), 4-biphenylboronic acid (0.045 g, 0.23 mmol) in THF (5 mL), and 2M sodium carbonate (0.29 mL). Treat the reaction with Pd(PPh3)4 (0.011 g, 0.01 mmol) and heat to 80° C. for 1 hour under N2. Cool the reaction, dilute with ethyl acetate, and wash with water. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify on silica with 100% ethyl acetate to afford 0.098 g (100%) of the titled product. Rf=0.44 (100% ethyl acetate). MS (m/z): 515 (M+).

Workup

  1. customPurge with N2
  2. additionTreat
  3. temperatureCool
  4. customthe reaction
  5. washwash with water
  6. dry with materialDry the organic layer with Na2SO4
  7. customremove the solvent in vacuo
  8. customto afford crude product
  9. customPurify on silica with 100% ethyl acetate

Sources & evidence

ORD record
ord-6c6403c2ff664ee88e854d073d2f9684
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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