Hydrochloric Acid → HCID 68483615, 화합물

HRID 1875190노트

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HRID 1875190 반응식
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]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 68487527HCID 68487527, 화합물

생성물 1

HCID 68483615HCID 68483615, 화합물수율 82%

시약·촉매·용매 2

HCID 5946Tetraethylammonium Chloride촉매HCID 8857Ethyl Acetate용매2회

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9fc828084c1f466e92a45d445956f003
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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