Potassium Fluoride → HCID 25005261、化合物

HRID 2239435ノート

反応式

HRID 2239435 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.[C:20]([C:22]1[N:26]([CH3:27])[C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].[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:20]([C:22]1[N:26]([CH3:27])[C:25]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]3[CH2:15][CH2:14]3)(=[O:10])=[O:9])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=2)=[CH:24][CH:23]=1)#[N:21]

参加物

6

反応物 3

HCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 249483674-bromo-N-(cyclopropylmethyl)-2-(trifluoromethyl)benzenesulfonamide

生成物 1

HCID 25005261HCID 25005261、化合物収率 53%

試薬・触媒・溶媒 2

HCID 83681Tris(1,1-dimethylethyl)phosphine触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

In analogous manner to general procedure B, 4-bromo-N-(cyclopropylmethyl)-2-(trifluoromethyl)benzenesulfonamide (200 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-(cyclopropylmethyl)-2-(trifluoromethyl)-benzenesulfonamide (106 mg, 53%) was provided after purification. MS (ESI) m/z 383. HPLC purity 100.0% at 210-370 nm, 10.8 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. customdried flask under nitrogen
  2. additiondry THF (1.4 mL) was added

出典と根拠

ORDレコード
ord-d1fb1bb5d6c547c791e53a4537c46612
出典データセット
uspto-grants-2010_05
特許番号
US07723332B2

反応ノート

読み込み中…