1-Ethynyl-4-fluorobenzene → HCID 67047635, compound

HRID 606883Notes

Reaction equation

HRID 606883 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)#[CH:11]>C(NC(C)C)(C)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]#[C:11][C:2]2[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 2

HCID 5226271-Ethynyl-4-fluorobenzeneHCID 8171633-Bromo-5-methoxypyridine

Product 1

HCID 67047635HCID 67047635, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 7912DiisopropylamineSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 3-bromo-5-methoxypyridine (1.0 g, 5.35 mmol) in diisopropylamine (17 mL) and toluene (10 mL) under nitrogen. Add tetrakis(triphenylphosphine)palladium (0.200 g, 0.16 mmol). Heat at 60° C. and add 1-ethynyl-4-fluorobenzene (642 mg, 5.35 mmol) and copper (I) iodide (20 mg, 0.11 mmol). After 20 h, concentrate, and purify using silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes, to give the title compound (720 mg, 60%).

Workup

  1. concentrationconcentrate
  2. custompurify
  3. washeluting with 30:70 ethyl acetate

Sources & evidence

ORD record
ord-bbbf3e46b1bd4b3486c0151705f240b9
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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