3-Butyn-1-OL → HCID 90417779, compound

HRID 633588Notes

Reaction equation

HRID 633588 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12]([C:13]3[CH:18]=[C:17]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=3[F:24])=[CH:11][N:10]([CH3:25])[C:5]2=[C:6]([O:8][CH3:9])[N:7]=1.[CH2:26]([OH:30])[CH2:27][C:28]#[CH:29]>O1CCCC1.C(N(CC)CC)C.[Cu]I>[CH2:22]([S:19]([C:17]1[CH:16]=[CH:15][C:14]([F:24])=[C:13]([C:12]2[C:4]3[C:5](=[C:6]([O:8][CH3:9])[N:7]=[C:2]([C:29]#[C:28][CH2:27][CH2:26][OH:30])[CH:3]=3)[N:10]([CH3:25])[CH:11]=2)[CH:18]=1)(=[O:21])=[O:20])[CH3:23]

Participants

6

Reactant 2

HCID 135663-Butyn-1-OLHCID 90417017HCID 90417017, compound

Product 1

HCID 90417779HCID 90417779, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of Example 126A (300 mg, 0.702 mmol), but-3-yn-1-ol (63.8 μl, 0.843 mmol), Pd(dppf)CH2Cl2 (57.3 mg, 0.070 mmol), and copper(I) iodide (13.4 mg, 0.070 mmol) in tetrahydrofuran (9 mL) and triethylamine (3 mL) was purged with nitrogen and then stirred at 70° C. in a sealed tube for 2.5 hours. The mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified on silica gel column (0-8% MeOH in dichloromethane) to give the title compound (200 mg, 68.4% yield)

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  3. washThe combined organic phases were washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel column (0-8% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-5268e56aec1945dc8515faaaf01af3ed
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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