Potassium Fluoride → 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N,N-dimethyl-2-(trifluoromethyl)benzenesulfonamide

HRID 2239419노트

반응식

HRID 2239419 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=1.[C:18]([C:20]1[N:24]([CH3:25])[C:23](B(O)O)=[CH:22][CH:21]=1)#[N:19].[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:18]([C:20]1[N:24]([CH3:25])[C:23]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=2)=[CH:22][CH:21]=1)#[N:19]

참가 물질

6

반응물 3

HCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 68410001Benzenesulfonamide, 4-bromo-N,N-dimethyl-2-(trifluoromethyl)-

생성물 1

HCID 250049194-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N,N-dimethyl-2-(trifluoromethyl)benzenesulfonamide수율 58%

시약·촉매·용매 2

HCID 83681Tris(1,1-dimethylethyl)phosphine촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

According to general procedure B, 4-bromo-N,N-dimethyl-2-(trifluoromethyl)benzenesulfonamide (186 mg, 0.56 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (100 mg, 0.67 mmol), potassium fluoride (107 mg, 1.85 mmol), and tris(dibenzylideneacetone)dipalladium(0) (14 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.4 mL) was added. Tri-t-butylphosphine (83 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-dimethyl-2-(trifluoromethyl)benzenesulfonamide (115 mg, 58%) was provided after purification. MS (ESI) m/z 357. HPLC purity 98.4% at 210-370 nm, 10.4 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.

후처리

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

출처 및 근거

ORD 기록
ord-60dea2f0630741a9b12ba5cabfaa8917
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723332B2

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