1,2-Dimethoxyethane → HCID 53975108, compound

HRID 363193Notes

Reaction equation

HRID 363193 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[OH-].[Ba+2].[OH-].COCCOC.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O>O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 5642162-Bromo-5-methylpyridineHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 6093286Barium hydroxide

Product 1

HCID 53975108HCID 53975108, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 2 bromo-5-methyl pyridine (1.81 g, 10.53 mmol) and barium hydroxide (4.97 g, 15.78 mmol) in water (15 mL) was added DME (80 mL). This mixture was treated sequentially with 2-(trifluoromethyl)phenylboronic acid (2.00 g, 10.53 mmol) and palladium tetrakis(triphenylphosphine) (553 mg, 0.48 mmol) and the mixture warmed to 80° C. for 48 hours. Water (100 mL) was added and the pH of the solution was adjusted to 10 and extracted with EtOAc (3×200 mL).

Workup

  1. extractionextracted with EtOAc (3×200 mL)

Sources & evidence

ORD record
ord-4361350d343a49b997087a736f033ea0
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Reaction notes

Loading…