o-Iodoanisole → HCID 11055160, compound

HRID 1669509Notes

Reaction equation

HRID 1669509 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21].Cl.CN(C)CC(O)=O>O1CCOCC1.[Cu]I>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][C:18]([O:12][C:9]2[CH:10]=[CH:11][C:6]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)=[CH:7][CH:8]=2)=[CH:19][CH:14]=1

Participants

6

Reactant 3

HCID 68257o-IodoanisoleHCID 75605N,N-Dimethylglycine hydrochlorideHCID 2238404-(1,3-Thiazol-2-yl)phenol

Product 1

HCID 11055160HCID 11055160, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of product from step 3 (0.55 g, 3.1 mmol), iodoanisole (1.1 g, 4.6 mmol), CsCO3 (3.0 g, 9.2 mmol), N,N-dimethylglycine HCl (0.43 g, 3.1 mmol) and CuI (0.3 g, 1.5 mmol) in dioxane (40 mL) was heated to 100° C. for 3 days. After the solids were filtered off, the filtrate was partitioned with EtOAc/H2O, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a column chromatography on silica gel to yield the title compound (0.75 g, 90%). 1HNMR (400 MHz, CDCl3) δ 3.82 (s, 3H), 6.90 (d, J=8 Hz, 2H), 6.97 (d, J=8.8 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 7.28 (d, J=3.6 Hz, 1H), 7.81 (d, J=3.6 Hz, 1H), 7.90 (d, J=8.8 Hz, 2H), MS m/z 284 (M+1).

Workup

  1. filtrationAfter the solids were filtered off
  2. customthe filtrate was partitioned with EtOAc/H2O
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-4e34b6edb6f348b99b28379ab8175ce8
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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