Potassium Fluoride → HCID 25006360, compound

HRID 2239479Notes

Reaction equation

HRID 2239479 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[C:4]([O:16][C:17]([F:20])([F:19])[F:18])[CH:3]=1.[C:21]([C:23]1[N:27]([CH3:28])[C:26](B(O)O)=[CH:25][CH:24]=1)#[N:22].[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].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:21]([C:23]1[N:27]([CH3:28])[C:26]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[C:4]([O:16][C:17]([F:20])([F:19])[F:18])[CH:3]=2)=[CH:25][CH:24]=1)#[N:22]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 68479618HCID 68479618, compound

Product 1

HCID 25006360HCID 25006360, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

According to general procedure B, 4-bromo-N,N-diethyl-2-(trifluoromethoxy)benzenesulfonamide (225 mg, 0.59 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (107 mg, 0.71 mmol), potassium fluoride (113 mg, 1.95 mmol), and tris(dibenzylideneacetone)dipalladium (0) (15 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.4 mL) was added. Tri-t-butylphosphine (89 μL, 0.02 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N,N-diethyl-2-(trifluoromethoxy)benzenesulfonamide (98 mg, 42%) was provided after purification. MS (ESI) m/z 401. HPLC purity 100.0% at 210-370 nm, 10.3 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Workup

  1. customwere placed in an oven
  2. customdried flask under nitrogen
  3. additiondry THF (1.4 mL) was added

Sources & evidence

ORD record
ord-708768d6fd2b4165bf5935b2abbba834
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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