Diisopropylethylamine → HCID 18672418、化合物

HRID 1058239ノート

反応式

HRID 1058239 の反応式
CCN(C(C)C)C(C)C.Cl.[F:11][C:12]1([F:16])[CH2:15][NH:14][CH2:13]1.Br[CH2:18][C:19]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:20]=1[C:21]#[N:22]>C(Cl)Cl>[Cl:27][C:24]1[CH:25]=[CH:26][C:19]([CH2:18][N:14]2[CH2:15][C:12]([F:16])([F:11])[CH2:13]2)=[C:20]([CH:23]=1)[C:21]#[N:22]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 126680522-(Bromomethyl)-5-chlorobenzonitrile

生成物 1

HCID 18672418HCID 18672418、化合物収率 55.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

DIEA (0.196 mL, 1.12 mmol) was added to a stirred mixture of 3,3-difluoroazetidine hydrochloride (64.8 mg, 0.50 mmol) and 2-bromomethyl-5-chlorobenzonitrile (121.0 mg, 0.52 mmol) in CH2Cl2 (7 mL). After 16 h the reaction was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated. The residue was partitioned between 1N HCl and ether. The aqueous layer was made neutral with NaHCO3 and was extracted with CH2Cl2. The organic layer was dried with Na2SO4 and then evaporated to give 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzonitrile (67.8 mg) as a glass: 1H NMR (CDCl3, 400 MHz) δ 3.68 (t, J=11.9 Hz. 4H), 3.93 (s, 2H), 7.54 (m, 2H), 7.63 (d, J=2.2 Hz, 1H).

後処理

  1. customAfter 16 h the reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was partitioned between 1N HCl and ether
  6. extractionwas extracted with CH2Cl2
  7. dry with materialThe organic layer was dried with Na2SO4
  8. customevaporated

出典と根拠

ORDレコード
ord-66db6927a39e435687a3f4545f42d76d
出典データセット
uspto-grants-2003_02
特許番号
US06515011B2

反応ノート

読み込み中…