Sodium Carbonate → HCID 57940589, compound

HRID 1437041Notes

Reaction equation

HRID 1437041 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][N:9]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)(=O)=O.[F:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C(Cl)Cl.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>[F:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=1[C:7]1[CH2:8][N:9]([S:19]([C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)(=[O:20])=[O:21])[CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 57940593HCID 57940593, compound

Product 1

HCID 57940589HCID 57940589, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

To a flame dried flask equipped with stir bar was added crude 1-[(4-nitrophenyl)sulfonyl]-5-phenyl-1,2,5,6-tetrahydropyridin-3-yl trifluoromethanesulfonate (1-5) (376 mg, 0.76 mmol), 2,5-difluorophenyl boronic acid (240 mg, 1.5 mmol), and Na2CO3 (243 mg, 2.3 mmol). The solids were dissolved in 5 mL 4:1 DME/H2O and degassed with N2. Pd(PPh3)4 (9 mg, 0.008 mmol) was added and the reaction was sealed under N2 and heated to 90 C for 2 h. Upon completion, the reaction was diluted with CH2Cl2, washed with 5% NaHCO3 and dried over MgSO4. Following filtration, the organic layer was concentrated and purified via ISCO (SiO2, 0-50% EtOAc/hexanes gradient) to provide 5-(2,5-difluorophenyl)-1-[(4-nitrophenyl)sulfonyl]-3-phenyl-1,2,3,6-tetrahydropyridine (1-6). 1H NMR (300 MHz, CDCl3) δ 8.35 (d, J=8.8 Hz, 2H), 7.94 (d, J=8.8 Hz, 2H), 7.34 (in, 5H), 7.20 (m, 1H), 7.02 (m, 2H), 6.09 (s, 1H), 4.27 (m, 1H), 3.94 (m, 1H), 3.82 (m, 2H), 2.86 (dd, J=12.0, 8.0 Hz, 1H); MS 457.3 found 457.5 (M+H+) required.

Workup

  1. customTo a flame dried flask
  2. customequipped
  3. customdegassed with N2
  4. customthe reaction was sealed under N2
  5. temperatureheated to 90 C for 2 h
  6. washwashed with 5% NaHCO3
  7. dry with materialdried over MgSO4
  8. filtrationfiltration
  9. concentrationthe organic layer was concentrated
  10. custompurified via ISCO (SiO2, 0-50% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-a7f7ef2e378a4b4aa272189fb832ec1e
Source dataset
uspto-grants-2009_11
Patent number
US07622468B2

Reaction notes

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