Tetrahydrofuran → N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide

HRID 1036093ノート

反応式

HRID 1036093 の反応式
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.C1COCC1.[F:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[NH2:9][C:3]1[N:4]=[C:5]([NH:8][C:25]([C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[F:22])=[O:26])[CH:6]=[CH:7][C:2]=1[Br:1]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 14158683-Bromopyridine-2,6-diamine

生成物 1

HCID 58487036N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide収率 57%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of 3-bromo-2,6-diaminopyridine (60) (564 mg, 3 mmol), triethyl amine (0.54 ml) in DCM (6 ml)/THF (4 ml) was cooled down to −78° C. A solution of 2-fluorobenzoyl chloride (362 μl, 3.03 mmol) in 2 ml DCM was added dropwise within 10 min. The resulting reaction mixture was stirred at −78° C. for 1 h before slowly warm up to r.t. After stirred at r.t. for 3 h, the reaction quenched with aq NaHCO3 solution. 200 ml EA were added. Org. phase was washed with brine, dried over sodium sulfate, concentrated. The light yellow solid residue was triturated with DCM (ca. 15 ml), filtered and dried to give 530 mg N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61) as white solid. (purity>95%, yield: 57%).

後処理

  1. customThe resulting reaction mixture
  2. temperaturebefore slowly warm up to r.t
  3. stirringAfter stirred at r.t. for 3 h
  4. customthe reaction quenched with aq NaHCO3 solution
  5. addition200 ml EA were added
  6. washphase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe light yellow solid residue was triturated with DCM (ca. 15 ml)
  10. filtrationfiltered
  11. customdried

出典と根拠

ORDレコード
ord-cbff9cb88fc74f5c855f30c367f1ead2
出典データセット
uspto-grants-2013_10
特許番号
US08546403B2

反応ノート

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