Potassium Phosphate, Tribasic → (3-Fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methanamine

HRID 711276ノート

反応式

HRID 711276 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][C:3]=1[F:10].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[C:17](B(O)O)[CH:16]=[CH:15][N:14]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(O)CC>[F:10][C:3]1[C:2]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([C:12]([F:23])([F:22])[F:11])[CH:18]=2)=[N:7][CH:6]=[C:5]([CH2:8][NH2:9])[CH:4]=1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 451588802-(Trifluoromethyl)pyridine-4-boronic acidHCID 53395621(6-Chloro-5-fluoropyridin-3-YL)methanamine

生成物 1

HCID 67208645(3-Fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methanamine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6568(+-)-2-Butanol溶媒

反応条件

温度
100 °C

実験手順

To a flask containing (6-chloro-5-fluoropyridin-3-yl)methanamine 84-1 (353 mg, 2.20 mmol), 2-(trifluoromethyl)pyridin-4-ylboronic acid 33-1 (418 mg, 2.20 mmol), Pd(OAc)2 (29 mg, 0.11 mmol), S-Phos (91 mg, 0.22 mmol) and potassium phosphate (1.40 g, 6.60 mmol) under Argon was added 2-butanol (4 mL). The mixture was stirred at 100° C. for 10 hours. After cooling to room temperature, the mixture was filtered through celite cake. The filtrate was diluted with ethyl acetate, washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, and eluted with 5% methanol containing ˜7N ammonia in dichloromethane to give (3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 84-2 as a pale yellow solid. MS m/z 268.1 (M+1)

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite cake
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 5% methanol containing ˜7N ammonia in dichloromethane

出典と根拠

ORDレコード
ord-24692876f15b4798ab880b7f9b3e0fe1
出典データセット
uspto-grants-2015_11
特許番号
US09181235B2

反応ノート

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