Nitrogen → (S)-6-Chloro-N-[1-(4-fluorophenyl)ethyl]pyridine-2-amine

HRID 75926

反応式

HRID 75926 の反応式
C1(C2C=CC=CC=2)C=CC=CC=1C(P(C)C)P(C)C.CC(C)([O-])C.[Na+].N#N.Cl[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[N:30]=1.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C@@H:43]([NH2:45])[CH3:44])=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:35][C:31]1[N:30]=[C:29]([NH:45][C@H:43]([C:40]2[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=2)[CH3:44])[CH:34]=[CH:33][CH:32]=1

参加物

8

反応物 5

HCID 947NitrogenHCID 169892,6-DichloropyridineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 23676156Sodium t-butoxideHCID 86620606(Biphenyl-2-ylmethylene)bis(dimethylphosphine)

生成物 1

HCID 86620619(S)-6-Chloro-N-[1-(4-fluorophenyl)ethyl]pyridine-2-amine収率 68%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

To a 25 ml round bottom flask was added Pd(OAc)2 (45 mg, 0.2 mmol), (biphenyl-2-ylmethylene)bis(dimethylphosphine) (120 mg, 0.4 mmol) and sodium tert-butoxide (480 mg, 5.0 mmol). The flask was sealed and refilled with N2. To the mixture was added a solution of 2,6-dichloropyridine (300 mg, 2.0 mmol) and [(1S)-1-(4-fluorophenyl)ethyl]amine (306 mg, 2.2 mmol) in toluene (4 ml). The reaction mixture was heated at 85° C. overnight. The solvent was removed and EtOAc was added and the mixture was washed with brine and was concentrated. Flash chromatography (10-40% EtOAc in hexanes) gave the title compound (339 mg, 68%). 1H NMR (CDCl3) δ 1.55 (m, 3H), 4.66 (m, 1H), 5.07 (br s, 1H), 6.01 (m, 1H), 6.54 (m, 1H), 7.00 (m, 2H), 7.25 (m, 3H).

後処理

  1. customThe flask was sealed
  2. customThe solvent was removed
  3. additionEtOAc was added
  4. washthe mixture was washed with brine
  5. concentrationwas concentrated

出典と根拠

ORDレコード
ord-b1d446cfe13e4ede88852f82e5308c9a
出典データセット
uspto-grants-2014_09
特許番号
US08835465B2

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