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

HRID 1878728Notes

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

Participants

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

customwas sparged with argon for 10 min
customThe reaction mixture was partitioned between EtOAc and 5% NaHCO3
customThe organic residue was purified on 40 grams of silica eluting with 20-60% EtOAc/hexane
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

Loading…