Potassium Fluoride → HCID 69109369, compound

HRID 1591833Notes

Reaction equation

HRID 1591833 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][S:9]2(=[O:14])=[O:13])=[CH:4][CH:3]=1.[CH3:15][N:16]1[C:20]([C:21]#[N:22])=[CH:19][CH:18]=[C:17]1B(O)O.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:13]=[S:9]1(=[O:14])[CH2:10][CH2:11][CH2:12][N:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:17]2[N:16]([CH3:15])[C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 125442182-(4-Bromophenyl)-1lambda~6~,2-thiazolidine-1,1-dione

Product 1

HCID 69109369HCID 69109369, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
25 °C

Procedure

2-(4-Bromophenyl)isothiazolidine 1,1-dioxide (0.56 g, 2.0 mmol), 1-methyl-5-cyano-2-pyrroleboronic acid (0.36 g, 2.4 mmol), KF (0.38 g, 6.6 mmol), and Pd2(dba)3 (48 mg, 0.05 mmol) were added to a 50 mL round bottom flask under nitrogen. The flask was sealed and purged with nitrogen for 5 minutes. THF (5 mL) was added and the mixture was purged with nitrogen. A solution of tri-t-butylphosphine (10% wt in hexanes) (0.3 mL, 0.1 mmol) was added via syringe and the mixture was stirred vigorously at 25° C. for 16 hours. The mixture was diluted with EtOAc, filtered through a plug of silica gel, washed with 200 mL of EtOAc and concentrated to give a crude brown/black semi-solid. Purification via Isco chromatography (the Redisep® column, silica, gradient 5%-100% ethyl acetate in hexane) afforded 5-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile as a white solid (54 mg).

Workup

  1. customThe flask was sealed
  2. custompurged with nitrogen for 5 minutes
  3. additionTHF (5 mL) was added
  4. customthe mixture was purged with nitrogen
  5. additionA solution of tri-t-butylphosphine (10% wt in hexanes) (0.3 mL, 0.1 mmol) was added via syringe
  6. additionThe mixture was diluted with EtOAc
  7. filtrationfiltered through a plug of silica gel
  8. washwashed with 200 mL of EtOAc
  9. concentrationconcentrated
  10. customto give a crude brown/black semi-solid
  11. customPurification via Isco chromatography (the Redisep® column, silica, gradient 5%-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c7ea95995ada4dbe87bbd74840b65755
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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