Dichloromethane → 2-{[6-(1-Benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}acetonitrile

HRID 1359224Notes

Reaction equation

HRID 1359224 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])=[C:7]([O:13][CH2:14][C:15]#[N:16])[CH:6]=[CH:5]2.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1B(O)O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])=[C:7]([O:13][CH2:14][C:15]#[N:16])[CH:6]=[CH:5]2

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 181827902-[(6-Bromo-1-methyl-2-naphthyl)oxy]acetonitrile

Product 1

HCID 181827852-{[6-(1-Benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}acetonitrile

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Following the procedure described in Step 1 of Example 1, 2-[(6-bromo-1-methyl-2-naphthyl)oxy]acetonitrile (4.93 g, 17.9 mmol) was coupled to 2-benzofuranboronic acid (3.58 g, 22.1 mmol) using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.452 g, 0.553 mmol) and potassium carbonate (3.75 g, 27.1 mmol) in dioxane (130 mL) and water (13 mL). Purification by flash chromatography using 3-9% ethyl acetate in hexane as an eluant yielded 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}acetonitrile a light yellow solid (3.03 g), mp 143-145° C., 1HNMR (300 MHz, DMSO-d6): δ8.45 (s, 1H), 7.95-8.15 (m, 3H), 7.7 (t, 2H, J=7.3 Hz), 7.5-7.6 (m, 2H), 7.2-7.4 (m, 2H), 5.35 (s, 2H), and 2.55 ppm (s, 3H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-6520d33f8d3e4985abd79cae89a68125
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

Loading…