N-methyl-2-pyrrolidone → 2-(Morpholin-4-yl)-3-trifluoromethyl-5-cyanopyridine

HRID 1820986ノート

反応式

HRID 1820986 の反応式
[N:1]1([C:7]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10](Br)=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:18][N:19]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:1]1([C:7]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:18]#[N:19])=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

参加物

6

反応物 2

HCID 13387N-methyl-2-pyrrolidoneHCID 688525644-[5-BRomo-3-(trifluoromethyl)pyridin-2-yl]morpholine

生成物 1

HCID 688505062-(Morpholin-4-yl)-3-trifluoromethyl-5-cyanopyridine

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

A mixture of 160 mg (0.63 mmol) of 2-(morpholin-4-yl)-3-trifluoromethyl-5-bromopyridine (from Step C), 117 mg (1.0 mmol) of zinc cyanide, 20.1 mg (0.22 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 48.7 mg (0.088) mmol of 1,1′-bis(diphenylphosphino)ferrocene in 2 mL of N-methylpyrrolidinone under argon was stirred at 100° C. for 1 h. The mixture was cooled and partitioned between ether and water. The organic layer was dried and concentrated. Chromatography on a Biotage 40S cartridge using 9:1 v/v hexanes/ether then 17:3 v/v hexanes/ether as the eluant afforded 87 mg of the title compound: ESI-MS (m/z) 258.2; HPLC A: 3.04 min.

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between ether and water
  3. customThe organic layer was dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-e8657ee4ac0048c6ac4882b9e1e8d85c
出典データセット
uspto-grants-2009_10
特許番号
US07605171B2

反応ノート

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