Potassium Phosphate, Tribasic → 4-Amino-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridine-2-carbonitrile

HRID 1481593ノート

反応式

HRID 1481593 の反応式
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O>O1CCOCC1.CCOC(C)=O.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:1][C:2]1[CH:7]=[C:6]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([F:34])([F:33])[F:22])[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12]

参加物

8

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 552704134-Amino-6-chloro-3-nitropicolinonitrile

生成物 1

HCID 674111964-Amino-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridine-2-carbonitrile

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 12976736Bis(ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane);iron(2+)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A solution of 4-amino-6-chloro-3-nitro-pyridine-2-carbonitrile (186 mg, 0.937 mmol) in 1,4-dioxane (5 mL) was treated with K3PO4 (1.00 g, 5.10 mmol), 2-trifluoromethylphenylboronic acid (178 mg, 0.937 mmol), 1,1′-bis(di-tert-butylphosphino)ferrocene (60.5 mg, 0.128 mmol) and Pd(OAc)2 (28.6 mg, 0.128 mmol). The resulting mixture was stirred 80° C. overnight. The cooled mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The aqueous layer was extracted twice with EtOAc (30 mL) and the combined extracts were dried over MgSO4 and concentrated in vacuo. The resulting residue was purified on silica (0:100-100:0 EtOAc-hexanes) to yield 4-amino-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridine-2-carbonitrile. 1H-NMR (400 MHz, CDCl3) δ: 7.79 (m, 1H), 7.67 (m, 4H), 7.52 (m, 1H), 7.04 (s, 1H).

後処理

  1. washwashed with water (50 mL)
  2. extractionThe aqueous layer was extracted twice with EtOAc (30 mL)
  3. dry with materialthe combined extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified on silica (0:100-100:0 EtOAc-hexanes)

出典と根拠

ORDレコード
ord-e306171e1f9f49a180703ac30d95b366
出典データセット
uspto-grants-2016_08
特許番号
US09409915B2

反応ノート

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