Sodium Carbonate → HCID 67480518, compound

HRID 509536Notes

Reaction equation

HRID 509536 reaction equation
[C:1]([O:5][C:6]([N:8]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:9]1[C:14]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:22][CH:21]=3)=[N:17][N:16]=2)=[CH:13][C:12](Br)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:44]([S:47]([C:50]1[CH:55]=[CH:54][C:53](B2OC(C)(C)C(C)(C)O2)=[CH:52][CH:51]=1)(=[O:49])=[O:48])([CH3:46])[CH3:45].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:9]1[C:14]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:22][CH:21]=3)=[N:17][N:16]=2)=[CH:13][C:12]([C:53]2[CH:52]=[CH:51][C:50]([S:47]([CH:44]([CH3:46])[CH3:45])(=[O:49])=[O:48])=[CH:55][CH:54]=2)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 532171014,4,5,5-Tetramethyl-2-[4-(propane-2-sulfonyl)phenyl]-1,3,2-dioxaborolaneHCID 67481718HCID 67481718, compound

Product 1

HCID 67480518HCID 67480518, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl N-[[4-[5-[2-[bis(tert-butoxycarbonyl)amino]-5-bromo-3-pyridyl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (120 mg, 0.1817 mmol) was dissolved in DMF (1.2 mL) and 2-(4-isopropylsulfonylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (84.57 mg, 0.2726 mmol) and Pd(PPh3)2Cl2 (7.516 mg, 0.01817 mmol) were added. 2M aqueous Na2CO3 (272.6 μL, 0.5451 mmol) was added and the reaction heated at 80° C. for 1 hour in a sealed tube. The reaction mixture was cooled to ambient temperature and diluted with EtOAc/water. The layers were separated and the aqueous layer extracted with EtOAc (×2). The combined organic extracts were washed with water (×3), brine (×2), dried (MgSO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (ISCO Companion™, 4 g column, 0-50% EtOAc/Petroleum ether) to give the impure sub-title compound as a yellow oil (136 mg). This was used directly in the next step with no further purification.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with EtOAc (×2)
  4. washThe combined organic extracts were washed with water (×3), brine (×2)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by column chromatography (ISCO Companion™, 4 g column, 0-50% EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-5dda399ee2c549c2b7cb5dc3888992a6
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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