Cesium carbonate → HCID 86757092, compound

HRID 1070331Notes

Reaction equation

HRID 1070331 reaction equation
[F:1][C:2]1[C:7]2[S:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:18]C.Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.[C:29]([O-:32])([O-:31])=[O:30].[Cs+].[Cs+].[C:35]([O-:38])([OH:37])=[O:36].[Na+]>CN(C=O)C>[C:35]([OH:37])(=[O:36])[C:29]([OH:32])=[O:31].[C:29]([OH:31])(=[O:30])[C:35]([OH:38])=[O:37].[F:1][C:2]1[C:7]2[S:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:13][CH:12]=3)=[C:10]([CH2:10][C:6]3[CH:7]=[CH:2][C:29]([O:32][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:4][CH:5]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 516892Sodium BicarbonateHCID 21182816HCID 21182816, compound

Product 1

HCID 86757092HCID 86757092, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-fluoro-2-[4-hydroxyphenyl]-6-methoxybenzo[b]thiophene (Part C; 550 mg, 2.0 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (375 mg, 2.2 mmol) and Cs2CO3 (1.65 g, 5.0 mmol) in 20 mL of DMF was heated at 80° C. for 5 h. The reaction mixture was cooled to ambient temperature and poured into saturated aqueous NaHCO3 solution (20 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were washed with H2O (2×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by radial chromatography (SiO2; 2% MeOH in CHCl3, saturated with NH4OH) afforded 598 mg (1.61 mmol; 80%) of the title compound as a yellow oil.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  2. washThe combined organics were washed with H2O (2×50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by radial chromatography (SiO2; 2% MeOH in CHCl3, saturated with NH4OH)

Sources & evidence

ORD record
ord-e3d614161fa2489db3b9af278334e60a
Source dataset
uspto-grants-2001_06
Patent number
US06251921B1

Reaction notes

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