Tris(1,1-dimethylethyl)phosphine → HCID 25006738, compound

HRID 2239495Notes

Reaction equation

HRID 2239495 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[C:4]([F:14])[CH:3]=1.[C:15]([C:17]1[N:21]([CH3:22])[C:20](B(O)O)=[CH:19][CH:18]=1)#[N:16].[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:15]([C:17]1[N:21]([CH3:22])[C:20]([C:2]2[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[C:4]([F:14])[CH:3]=2)=[CH:19][CH:18]=1)#[N:16]

Participants

6

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 59443491HCID 59443491, compound

Product 1

HCID 25006738HCID 25006738, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

According to general procedure B, 4-bromo-2,5-difluoro-N-methylbenzenesulfonamide (143 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-methylbenzenesulfonamide (24 mg). HPLC purity 87.6% at 210-370 nm, 8.4 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 C13H11F2N3O2S−H+, 310.04673; found (ESI-FTMS, [M−H]−1), 310.04692

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-61dad2b2af8740629f5ddb181ce0bc17
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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