Benzenesulfonamide, p-bromo-N-ethyl- → HCID 25004247、化合物

HRID 2239387ノート

反応式

HRID 2239387 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:14]([C:16]1[N:20]([CH3:21])[C:19](B(O)O)=[CH:18][CH:17]=1)#[N:15].[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:14]([C:16]1[N:20]([CH3:21])[C:19]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1)#[N:15]

参加物

6

反応物 4

HCID 74803Benzenesulfonamide, p-bromo-N-ethyl-HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acid

生成物 1

HCID 25004247HCID 25004247、化合物収率 13%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

In an analogous manner to general procedure B, 4-bromo-N-ethylbenzenesulfonamide (105 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. 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-ethylbenzenesulfonamide (15 mg, 13%) was provided after purification. MS (ESI) m/z 289. HPLC purity 100.0% at 210-370 nm, 9.6 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 (1.0 mL) was added

出典と根拠

ORDレコード
ord-f6298a01c79d4d1b9971ac99ff0d7b71
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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