Hydrochloric Acid → HCID 68483615、化合物

HRID 1875190ノート

反応式

HRID 1875190 の反応式
Br[C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:36])=[C:13]([CH2:18][NH:19][C:20]([C:22]3[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=[N:24][C:23]=3[Cl:35])=[O:21])[CH:14]=[CH:15][C:16]=2[Cl:17])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:42]([O:44]CC)=[CH2:43])CCC.Cl>[Cl-].C([N+](CC)(CC)CC)C.CCOC(C)=O>[C:42]([C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:36])=[C:13]([CH2:18][NH:19][C:20]([C:22]3[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[CH:25]=[N:24][C:23]=3[Cl:35])=[O:21])[CH:14]=[CH:15][C:16]=2[Cl:17])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1)(=[O:44])[CH3:43]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 68487527HCID 68487527、化合物

生成物 1

HCID 68483615HCID 68483615、化合物収率 82%

試薬・触媒・溶媒 2

HCID 5946Tetraethylammonium Chloride触媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of N-({3-[(3-bromo-5-cyanophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (500 mg, 0.814 mmol), tetraethylammoniumchloride (409 mg, 2.442 mmol) and dichlorobistriphenyl phosphinepalladium(II) (57.1 mg, 0.081 mmol) was added tributyl[1-(ethyloxy)ethenyl]stannane (0.302 mL, 0.894 mmol) and the reaction mixture was stirred at 80° C. overnight. The reaction mixture was cooled to RT, diluted with EtOAc and washed with water. The solvent was evaporated and the residue was dissolved in THF (7.00 mL) and HCl (1.0 M solution) (4 mL, 4.00 mmol) was added. The resulting mixture was stirred for 4 hours at RT. EtOAc was added and the organics were separated. The solvent was removed and the crude material was purifed via silica gel chromatography to give N-({3-[(3-acetyl-5-cyanophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (384 mg, 0.665 mmol, 82% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.08 (s, 1H), 7.90 (s, 1H), 7.70 (s, 1H), 7.33-7.49 (m, 3H), 5.59 (s, 2H), 4.61 (s, 2H), 3.49 (t, 2H), 2.60 (s, 3 H), 0.83 (t, 2H), −0.12-0.01 (m, 9H).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in THF (7.00 mL)
  5. stirringThe resulting mixture was stirred for 4 hours at RT
  6. customthe organics were separated
  7. customThe solvent was removed

出典と根拠

ORDレコード
ord-9fc828084c1f466e92a45d445956f003
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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