Sodium Carbonate → HCID 49835186, compound

HRID 451240Notes

Reaction equation

HRID 451240 reaction equation
Br[C:2]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][C:6]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:18][CH2:17]1)=[N:7]2.[C:27]([O-:30])([O-])=O.[Na+].[Na+]>CO.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>[C:12]([C:10]1[CH:9]=[C:8]2[C:3]([N:4]=[CH:5][C:6]([N:16]3[CH2:21][CH2:20][CH:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:18][CH2:17]3)=[N:7]2)=[C:2]([C:10]2[C:27](=[O:30])[NH:4][CH:3]=[CH:2][CH:11]=2)[CH:11]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 67127294HCID 67127294, compound

Product 1

HCID 49835186HCID 49835186, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

step 2—To a solution of 42 (0.040 g, 0.10 mmol) in MeOH and DCM (3 mL/1 mL), was added Na2CO3 (0.029 g, 0.27 mmol), 30 (0.012 g, 0.11 mmol) and Pd(PPh3)4 (0.010 g, 0.010 mmol). The reaction was irradiated in a microwave synthesizer at 115° C. for 30 min. The reaction was cooled, concentrated and partitioned between EtOAc/H2O (25 mL/25 mL). The aqueous layer was separated and washed EtOAc (2×25 mL). The combined organic extracts were washed with brine (25 mL), dried (Na2SO4), filtered and concentrated. The crude product was adsorbed onto SiO2 and purified by SiO2 chromatography eluting with 10% MeOH/DCM to afford 0.030 g (73%) of I-3.

Workup

  1. customThe reaction was irradiated in a microwave synthesizer at 115° C. for 30 min
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. custompartitioned between EtOAc/H2O (25 mL/25 mL)
  5. customThe aqueous layer was separated
  6. washwashed EtOAc (2×25 mL)
  7. washThe combined organic extracts were washed with brine (25 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by SiO2 chromatography
  12. washeluting with 10% MeOH/DCM
  13. customto afford 0.030 g (73%) of I-3

Sources & evidence

ORD record
ord-3d1427a215654314a58e70734bc397e9
Source dataset
uspto-grants-2013_07
Patent number
US08487103B2

Reaction notes

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