Potassium Acetate → HCID 67271785, compound

HRID 1696540Notes

Reaction equation

HRID 1696540 reaction equation
C([O-])(=O)C.[K+].[B:6].[B].[OH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH3:16][O:17][C:18]1[CH:36]=[CH:35][C:21]([CH2:22][N:23]2[C:32]3[C:27](=[CH:28][C:29](Br)=[CH:30][CH:31]=3)[CH:26]=[CH:25][C:24]2=[O:34])=[CH:20][CH:19]=1>CN(C=O)C.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]>[CH3:16][O:17][C:18]1[CH:36]=[CH:35][C:21]([CH2:22][N:23]2[C:32]3[C:27](=[CH:28][C:29]([B:6]4[O:15][C:12]([CH3:14])([CH3:13])[C:9]([CH3:11])([CH3:10])[O:8]4)=[CH:30][CH:31]=3)[CH:26]=[CH:25][C:24]2=[O:34])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 672720826-bromo-1-(4-methoxybenzyl)quinolin-2(1H)-oneHCID 86590017Pinacol diboron

Product 1

HCID 67271785HCID 67271785, compoundYield 647.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium acetate (54.3 g, 44 mmol), pinacol diboron (5.5 g, 22 mmol) and PdCl2(dppf) (0.60 mg, 0.73 mmol) were added sequentially to a solution 1-(4-methoxybenzyl)-6-bromoquinolin-2(1H)-one (5.0 g, 15 mmol) in DMF (70 mL). After flushing with N2, the reaction vessel was sealed and heated at 80° C. for 14 h and then partitioned between H2O and EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) concentrated and purified via column chromatography to yield 1-(4-methoxybenzyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one (38 g, 67% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.04 (brs, 1H), 7.86 (dd, J=1.2, and 8.4 Hz, 1H), 7.76 (d, J=9.6 Hz, 1H), 7.32 (d, J=9.2 Hz, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 6.80 (d, J=9.6 Hz, 1H), 5.52 (brs, 2H), 3.77 (s, 3H), 1.36 (s, 12H); LC-MS (EI) m/z: 392.3 (M+H+).

Workup

  1. customAfter flushing with N2
  2. customthe reaction vessel was sealed
  3. custompartitioned between H2O and EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-343459892b014659a5105aaaf2c5cbaf
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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