3-Bromopyridine → HCID 18677128, compound

HRID 1634124Notes

Reaction equation

HRID 1634124 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:8]#[C:9][CH:10]([OH:13])[CH2:11][CH3:12]>C(N(CC)CC)C.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.CSC.[Cu]Br>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:8]#[C:9][CH:10]([OH:13])[CH2:11][CH3:12])[CH:3]=1

Participants

6

Reactant 2

HCID 122863-BromopyridineHCID 929811-Pentyn-3-ol

Product 1

HCID 18677128HCID 18677128, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 2724234Bromo(thiobis(methane))copperCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-bromopyridine (12.0 g, 75.6 mmol) and 1-pentyn-3-ol (7.0 mL, 83.2 mmol) in triethylamine (150 mL) were added Pd(PPh3)4 (88 mg, 0.076 mmol) and copper(I) bromide dimethylsulfide (31 mg, 0.15 mmol). The mixture was heated at 70° C. for 5 hr, cooled to room temperature and filtered. The filter cake was washed with EtOAc (30 mL). The combined filtrate was concentrated to give 1-(3-pyridinyl)-1-pentyn-3-ol (12.2 g, 99%) as a dark oil.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe filter cake was washed with EtOAc (30 mL)
  4. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-ae335751c33c4e9484fe3ada2f4952f3
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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