Sodium Carbonate → HCID 21905377, compound

HRID 1247407Notes

Reaction equation

HRID 1247407 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][C:6]([CH2:7][NH:8][C:9](=[O:31])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:16][C:15]=2[F:30])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].Cl.Br[C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:31])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][C:17]([C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)=[CH:16][C:15]=2[F:30])[O:11][CH2:12][CH3:13])=[CH:32][CH:33]=1)#[N:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 21905505HCID 21905505, compound

Product 1

HCID 21905377HCID 21905377, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of (RS)-N-(4-cyano-benzyl)-2-[2,6-difluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-ethoxy-acetamide (300 mg) in 1,2-dimethoxyethane (8 ml) was added 4-bromopyridine hydrochloride (387 mg). A solution of sodium carbonate (210 mg) in water (2.1 ml) and dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium (II) (48 mg) were added. The mixture was stirred at 85° C. for 4 h and at rt overnight. After cooling to rt, ice water was added. The mixture was filtered and the filtrate was extracted with EtOAc. The org. phase was washed with brine, dried, filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 2:1=>EtOAc) to give (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-4-pyridin-4-yl-phenyl)-2-ethoxy-acetamide (189 mg). Off-white solid. MS 408.2 ([M+H]+)

Workup

  1. temperatureAfter cooling to rt
  2. filtrationThe mixture was filtered
  3. extractionthe filtrate was extracted with EtOAc
  4. washphase was washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 2:1=>EtOAc)

Sources & evidence

ORD record
ord-bb0bb012dc214bfca9c1c0e42f7b6fab
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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