Tris(1,1-dimethylethyl)phosphine → 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-methyl-2-(trifluoromethoxy)benzenesulfonamide

HRID 2239473ノート

反応式

HRID 2239473 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[C:4]([O:13][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+].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:18]([C:20]1[N:24]([CH3:25])[C:23]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[C:4]([O:13][C:14]([F:17])([F:16])[F:15])[CH:3]=2)=[CH:22][CH:21]=1)#[N:19]

参加物

6

反応物 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 594434404-bromo-N-methyl-2-(trifluoromethoxy)benzenesulfonamide

生成物 1

HCID 250059814-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-methyl-2-(trifluoromethoxy)benzenesulfonamide収率 28.8%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

According to general procedure B, 4-bromo-N-methyl-2-(trifluoromethoxy)benzenesulfonamide (200 mg, 0.59 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (107 mg, 0.71 mmol), potassium fluoride (113 mg, 1.95 mmol), and tris(dibenzylideneacetone)dipalladium (0) (15 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.4 mL) was added. Tri-t-butylphosphine (89 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-methyl-2-(trifluoromethoxy)benzenesulfonamide (61 mg, 28%) was provided after purification. MS (ESI) m/z 359. HPLC purity 99.6% 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.

後処理

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

出典と根拠

ORDレコード
ord-f69ad96f3e4e40abb16d9d195404f878
出典データセット
uspto-grants-2010_05
特許番号
US07723332B2

反応ノート

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