Tris(1,1-dimethylethyl)phosphine → 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile

HRID 1591834ノート

反応式

HRID 1591834 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[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]>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:19]2[N:20]([CH3:21])[C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)=[CH:3][C:4]=1[O:9][C:10]([F:13])([F:12])[F:11]

参加物

6

反応物 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 7373824-Bromo-2-(trifluoromethoxy)anilineHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acid

生成物 1

HCID 160505285-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile収率 71.1%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

4-Bromo-2-(trifluoromethoxy)aniline (1.3 g, 5.0 mmol), 5-cyano-1-methyl-1H-pyrrol-2-yl boronic acid (0.9 g, 6.0 mmol), potassium fluoride (0.96 g, 16.5 mmol), and tris(dibenzylideneacetone)dipalladium (0.12 g, 0.12 mmol) were placed in an oven dried flask under nitrogen and THF (12.5 mL) was added. Tri-t-butylphosphine (10 wt % in hexane) (0.356 mL, 0.24 mol) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica, rinsed with ethyl acetate, and concentrated. The crude product was pre-adsorbed onto the Celite™ reagent and purified via Isco chromatography (the Redisep® column, silica, gradient 5-30% ethyl acetate in hexane) to afford 1.0 g (71%) of 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile.

後処理

  1. customdried flask under nitrogen
  2. additionTHF (12.5 mL) was added
  3. filtrationThe reaction mixture was filtered through silica
  4. washrinsed with ethyl acetate
  5. concentrationconcentrated
  6. custompurified via Isco chromatography (the Redisep® column, silica, gradient 5-30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-ea220ee8fa194283bd03f23705775c9e
出典データセット
uspto-grants-2007_11
特許番号
US07291643B2

反応ノート

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