3-Bromopyridine → HCID 69463970, compound

HRID 1856642Notes

Reaction equation

HRID 1856642 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-99ea45fea3f74beebfd9e2ffd6d2eb0f
Source dataset
uspto-grants-2000_11
Patent number
US06143736

Reaction notes

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