4-Bromobenzenesulfonamide → HCID 59304407, compound

HRID 2239502Notes

Reaction equation

HRID 2239502 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]([C:14]1[N:18]([CH3:19])[C:17](B(O)O)=[CH:16][CH:15]=1)#[N:13].[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:12]([C:14]1[N:18]([CH3:19])[C:17]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1)#[N:13]

Participants

6

Reactant 4

HCID 696964-BromobenzenesulfonamideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acid

Product 1

HCID 59304407HCID 59304407, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

According to general procedure B, 4-bromobenzenesulfonamide (472 mg, 2.0 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (360 mg, 2.4 mmol), potassium fluoride (350 mg, 6.0 mmol), and tris(dibenzylideneacetone)-dipalladium (48 mg, 0.05 mmol) were placed in an oven dried flask under nitrogen and dry THF (5 mL) was added. Tri-t-butylphosphine (0.30 mL, 0.1 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)benzenesulfonamide (190 mg). MS (ES) m/z 261.8; HPLC purity 99.6% at 210-370 nm, 7.1 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 (5 mL) was added
  4. customPurification

Sources & evidence

ORD record
ord-a7d77e3878234505a075e84a2cc4b12f
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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