Sodium Carbonate → HCID 68104456, compound

HRID 509537Notes

Reaction equation

HRID 509537 reaction equation
[C:1]([O:5][C:6]([N:8]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[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](B2OC(C)(C)C(C)(C)O2)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:53]1[CH:58]=[CH:57][C:56]([S:59]([CH:62]([CH3:64])[CH3:63])(=[O:61])=[O:60])=[CH:55][N:54]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[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])([CH3:31])[CH3:32])=[CH:22][CH:21]=3)=[N:17][N:16]=2)=[CH:13][C:12]([C:53]2[CH:58]=[CH:57][C:56]([S:59]([CH:62]([CH3:64])[CH3:63])(=[O:60])=[O:61])=[CH:55][N:54]=2)=[CH:11][N:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 529881802-Bromo-5-(propane-2-sulfonyl)pyridineHCID 68104455HCID 68104455, compound

Product 1

HCID 68104456HCID 68104456, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

The reaction mixture from Method F Step 1 was diluted with DMF (2 mL) an 2-bromo-5-isopropylsulfonyl-pyridine [Compound I-7a; prepared according to Method F-1] (48 mg, 0.1817 mmol), Pd(PPh3)2Cl2 (6.263 mg, 0.01514 mmol) and 2M aqueous Na2CO3 (227.1 μL, 0.4542 mmol) were added. The reaction was degassed with nitrogen and stirred at 95° C. for 2 hours in a sealed tube. The reaction mixture was partitioned between EtOAc and brine and the aqueous layer extracted with EtOAc (×2). The combined organic extracts were washed with brine (×3), dried (MgSO4), filtered and concentrated in vacuo. The crude residue was used in the deprotection step without further purification.

Workup

  1. additionwere added
  2. customThe reaction was degassed with nitrogen
  3. customThe reaction mixture was partitioned between EtOAc and brine
  4. extractionthe aqueous layer extracted with EtOAc (×2)
  5. washThe combined organic extracts were washed with brine (×3)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was used in the deprotection step without further purification

Sources & evidence

ORD record
ord-1b174c5643ef4539a1f94921d30fae7d
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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