3-Bromopyridine → HCID 69463970, compound

HRID 1585825Notes

Reaction equation

HRID 1585825 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([C@@:10]1([OH:32])[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:20](=[O:22])[CH3:21])[CH2:11]1)#[CH:9]>>[OH:32][C@:10]1([C:8]#[C:9][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:20](=[O:22])[CH3:21])[CH2:11]1

Participants

3

Reactant 2

HCID 122863-BromopyridineHCID 10736101HCID 10736101, compound

Product 1

HCID 69463970HCID 69463970, compoundYield 16.2%

Conditions

Temperature
23 °C

Procedure

A solution of 3-bromopyridine (70 mg, 0.44 mmol), 3β-ethynyl-3α-hydroxy-5α-pregnan-20-one (150 mg, 0.44 mmol) in dry degassed diethylamine (1 mL) was stirred under argon at 23° C. Bis(triphenylphosphine)palladium chloride (10 mg) and CuI (5 mg) were added and the mixture was stirred at this temp. for 45 min. CH2Cl2 (4 mL) was added and the mixture was stirred at 23° C. for 1.5 hr. TLC showed 100% conversion of the starting material, hence, the solvent was removed and the residue was purified by chromatography on silica gel. Elution with hexane:acetone (3:1) gave 3α-hydroxy-3β-(3-pyridyl)ethynyl-5β-pregnan-20-one (30 mg) as a colorless solid; mp 230--35° C., TLC Rf (hexane:acetone 7:3)=0.24.

Workup

  1. customdegassed diethylamine (1 mL)
  2. additionBis(triphenylphosphine)palladium chloride (10 mg) and CuI (5 mg) were added
  3. stirringthe mixture was stirred at this temp
  4. additionCH2Cl2 (4 mL) was added
  5. stirringthe mixture was stirred at 23° C. for 1.5 hr
  6. customhence, the solvent was removed
  7. customthe residue was purified by chromatography on silica gel
  8. washElution with hexane:acetone (3:1)

Sources & evidence

ORD record
ord-7b009f324722435faa2eb940517b7986
Source dataset
uspto-grants-1999_08
Patent number
US05939545

Reaction notes

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