Tris(1,1-dimethylethyl)phosphine → HCID 25006741, compound

HRID 2239497Notes

Reaction equation

HRID 2239497 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:12][CH:13]([CH3:15])[CH3:14])(=[O:11])=[O:10])=[C:4]([F:16])[CH:3]=1.[C:17]([C:19]1[N:23]([CH3:24])[C:22](B(O)O)=[CH:21][CH:20]=1)#[N:18].[F-].[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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:17]([C:19]1[N:23]([CH3:24])[C:22]([C:2]2[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:12][CH:13]([CH3:15])[CH3:14])(=[O:11])=[O:10])=[C:4]([F:16])[CH:3]=2)=[CH:21][CH:20]=1)#[N:18]

Participants

6

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 68483705HCID 68483705, compound

Product 1

HCID 25006741HCID 25006741, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

According to general procedure B, 4-bromo-2,5-difluoro-N-isopropylbenzenesulfonamide (150 mg, 0.5 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (90 mg, 0.60 mmol), potassium fluoride (96 mg, 1.65 mmol), and tris(dibenzylideneacetone)dipalladium (12 mg, 0.013 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.3 mL) was added. Tri-t-butylphosphine (75 μL, 0.026 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. Purification afforded 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2,5-difluoro-N-isopropylbenzenesulfonamide (24 mg) HPLC purity 97.2% at 210-370 nm, 9.3 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. HRMS: calcd for C15H15F2N3O2S−H+, 338.07803; found (ESI-FTMS, [M−H]1−), 338.07811

Workup

  1. customwere placed in an oven
  2. customdried flask under nitrogen
  3. additiondry THF (1.3 mL) was added
  4. customPurification

Sources & evidence

ORD record
ord-6ff8c118f6464898b738e898f4f1a4c5
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

Loading…