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Sodium Carbonate → 1-(2-(Benzyloxy)ethyl)-5-phenylpyridin-2(1H)-one

HRID 1878728
Notes
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Reaction equation

HRID 1878728 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[CH:16]=[C:15](Br)[CH:14]=[CH:13][C:12]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[CH:16]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:12]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 598430091-(2-(Benzyloxy)ethyl)-5-bromopyridin-2(1H)-one

Product 1

HCID 598430561-(2-(Benzyloxy)ethyl)-5-phenylpyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 1-(2-(benzyloxy)ethyl)-5-bromopyridin-2(1 H)-one (350 mg, 1.14 mmol), phenylboronic acid (277 mg, 2.27 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (83 mg, 114 μmol), Na2CO3 (1.70 mL, 3.41-mmol) [2M], and DME (3 mL) was sparged with argon for 10 min then heated to 85° C. for 60 min. The reaction mixture was partitioned between EtOAc and 5% NaHCO3. The organic residue was purified on 40 grams of silica eluting with 20-60% EtOAc/hexane to give a colorless oil. MS (ESI pos. ion) m/z (MH+): 306. Calc'd exact mass for C20H19NO2: 305. 1H NMR (400 MHz, Chloroform-d) δ ppm 3.77-3.89 (m, 2 H) 4.19-4.30 (m, 2 H) 4.50 (s, 2 H) 6.58-6.73 (m, 1 H) 7.17-7.45 (m, 10H) 7.59-7.71 (m, 2 H).

Workup

  1. customwas sparged with argon for 10 min
  2. customThe reaction mixture was partitioned between EtOAc and 5% NaHCO3
  3. customThe organic residue was purified on 40 grams of silica eluting with 20-60% EtOAc/hexane
  4. customto give a colorless oil

Sources & evidence

ORD record
ord-3777b9f1500b4c29a9973a4cc28af952
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314087B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes