Sodium Carbonate → 3-Acetoxy-17-(3-pyridyl)estra-1,3,5[10],16-tetraene

HRID 1451365Notes

Reaction equation

HRID 1451365 reaction equation
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.FC(F)(F)S(O[C:18]1[C@:19]2([CH2:35][CH2:34][C@H:33]3[C@@H:24]([CH2:25][CH2:26][C:27]4[CH:28]=[C:29]([O:36][C:37](=[O:39])[CH3:38])[CH:30]=[CH:31][C:32]=43)[C@@H:21]2[CH2:22][CH:23]=1)[CH3:20])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:37]([O:36][C:29]1[CH:30]=[CH:31][C:32]2[C@@H:33]3[C@H:24]([C@H:21]4[C@@:19]([CH2:35][CH2:34]3)([CH3:20])[C:18]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)=[CH:23][CH2:22]4)[CH2:25][CH2:26][C:27]=2[CH:28]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 10478617HCID 10478617, compound

Product 1

HCID 103393193-Acetoxy-17-(3-pyridyl)estra-1,3,5[10],16-tetraene

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The method followed that described in Example 1(b), but using diethyl(3-pyridyl)borane (1.65 g, 11.2 mmol), 3-acetoxyestra-1,3,5[10],16-tetraen-17-yl trifluoromethanesulphonate (3.56 g, 8.0 mmol), THF (40 ml), bis(triphenylphosphine)palladium(II) chloride (56 mg, 0.08 mmol), and aqueous sodium carbonate (2M, 15 ml).

Sources & evidence

ORD record
ord-7e8cb078504c4aefb1b167037ef64889
Source dataset
uspto-grants-1997_02
Patent number
US05604213

Reaction notes

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