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Sodium Carbonate → N-{1-[6-(4-methoxyphenyl)pyridin-3-yl]-1-methylethyl}acetamide

HRID 386602
Notes
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Reaction equation

HRID 386602 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>CC(N(C)C)=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>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=2)=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 77231171N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide2×

Product 1

HCID 66865802N-{1-[6-(4-methoxyphenyl)pyridin-3-yl]-1-methylethyl}acetamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compound
Catalyst
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

The product from Step B, 1-B, (37.11 g, 174 mmol), 4-methoxyphenylboronic acid (47.7 g, 314 mmol) and bis(triphenylphosphine)palladium(II) chloride (6.12 g, 8.72 mmol) were suspended in DMA (325 mL) and aq. 2.0 M Na2CO3 (288 mL, 576 mmol). The atmosphere of the reaction vessel was evacuated/purged with N2 (3×) and the reaction mixture was heated at 90° C. over 3 h. The reaction mixture was cooled to rt and partitioned between EtOAc and H2O. The organic layer was separated, washed with H2O, saturated aq. NaCl, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was suspended in CH2Cl2 and the solid were isolated by vacuum filtration and dried under high vacuum. Alternative work-up: The reaction mixture was cooled to rt and diluted with H2O (1.85 L). The solids were collected by vacuum filtration rinsing with hexanes and dried under high vacuum. HPLC/MS: 285.0 (M+1); Rt=1.53 min.

Workup

  1. customThe atmosphere of the reaction vessel was evacuated/purged with N2 (3×)
  2. temperatureThe reaction mixture was cooled to rt
  3. custompartitioned between EtOAc and H2O
  4. customThe organic layer was separated
  5. washwashed with H2O, saturated aq. NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customthe solid were isolated by vacuum filtration
  10. customdried under high vacuum
  11. temperatureThe reaction mixture was cooled to rt
  12. additiondiluted with H2O (1.85 L)
  13. filtrationThe solids were collected by vacuum filtration
  14. washrinsing with hexanes
  15. customdried under high vacuum

Sources & evidence

ORD record
ord-7c6105226b6e404e96a8b9738a49bfc9
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372857B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes