Water → 1-(3-(Benzofuran-2-yl)pyridin-4-yl)ethanol

HRID 1897574Notes

Reaction equation

HRID 1897574 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]([OH:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].O.C(Cl)Cl>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].CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]([OH:22])[CH3:21]

Participants

8

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 667978531-(3-Bromopyridin-4-yl)ethanol

Product 1

HCID 532368511-(3-(Benzofuran-2-yl)pyridin-4-yl)ethanolYield 23.4%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of benzofuran-2-boronic acid (178 mg, 1.100 mmol), 1-(3-bromopyridin-4-yl)ethanol (202 mg, 1 mmol), sodium carbonate 2N in water (1 mL, 2.000 mmol), PdCl2(dppf).CH2Cl2 adduct (40.8 mg, 0.050 mmol) in DMF (5 mL) was heated to 100° C. for 3 hrs. The mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (25M column, 20-60% EtOAc/heptane, v/v) giving the title compound (56 mg, 23%) as yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.56 (d, J=6.4 Hz, 3H), 5.53 (q, J=6.4 Hz, 1H), 7.03 (d, J=0.7 Hz, 1H), 7.31 (td, J=7.3, 0.9 Hz, 1H), 7.38 (td, J=8.0, 1.2 Hz, 1H), 7.54 (dd, J=8.2, 0.7 Hz, 1H), 7.66 (dd, J=7.6, 0.6 Hz, 1H), 7.85 (d, J=5.4 Hz, 1H), 8.63 (bs, 1H), 8.91 (bs, 1H). LC-MS (M+1) 240.2, t=1.25 min.

Workup

  1. customThe mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via Biotage (25M column, 20-60% EtOAc/heptane, v/v)

Sources & evidence

ORD record
ord-698f1f4a3f954d54ab4655b26891881b
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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