Tris(1,1-dimethylethyl)phosphine → HCID 25003913, compound

HRID 2239383Notes

Reaction equation

HRID 2239383 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:13]([C:15]1[N:19]([CH3:20])[C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].[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:13]([C:15]1[N:19]([CH3:20])[C:18]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1)#[N:14]

Participants

6

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 1012154-bromo-N-methylbenzene-1-sulfonamideHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acid

Product 1

HCID 25003913HCID 25003913, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

4-Bromo-N-methylbenzenesulfonamide (100 mg, 0.40 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (72 mg, 0.48 mmol), potassium fluoride (76 mg, 1.3 mmol), and tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.0 mL) was added. Tri-t-butylphosphine (60 μL, 0.02 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica and rinsed with ethyl acetate. The solvent was concentrated in vacuo to provide the crude product. The crude product was pre-adsorbed onto the Celite® reagent and purified via Isco chromatography (the Redisep™ column, silica, gradient 5-50% ethyl acetate in hexane) to afford 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-methylbenzenesulfonamide (28 mg, 25%). MS (ESI) m/z 275. HPLC purity 100.0% at 210-370 nm, 9.0 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. customdried flask under nitrogen
  2. additiondry THF (1.0 mL) was added
  3. filtrationThe reaction mixture was filtered through silica
  4. washrinsed with ethyl acetate
  5. concentrationThe solvent was concentrated in vacuo
  6. customto provide the crude product
  7. custompurified via Isco chromatography (the Redisep™ column, silica, gradient 5-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-06f0b7a59ad541378bb91c6a372bf0df
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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