1,4-Dioxane → (S)-tert-butyl ((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

HRID 509330

반응식

HRID 509330 반응식
Br[C:2]1[C:3]([C@@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.O1CCOCC1.[CH2:33]([Sn](CCCC)(CCCC)C#CC)[CH2:34][CH2:35]C>CCOC(C)=O>[C:33]([C:2]1[C:3]([C@@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)#[C:34][CH3:35]

참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 71164782(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

생성물 1

HCID 86687953(S)-tert-butyl ((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a microwave vial containing (S)-tert-butyl ((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate (500 mg, 1.159 mmol) and a stir bar was added 1,4-dioxane (6 mL). To this solution was added tetrakis(triphenyl-phosphine)palladium(0) (67.0 mg, 0.058 mmol, 0.05 eq) and tributyl(prop-1-yn-1-yl)stannane (458 mg, 1.391 mmol, 1.2 eq). The vial was capped and irradiated in a microwave at 120° C. for 20 min. The vial was allowed to cool, diluted with hexanes (5 mL) and loaded directly to a normal phase silica gel column (80 g ISCO, 0 to 40% EtOAc in hexanes) to provide (S)-tert-butyl ((3-(prop-1-yn-1-yl)-pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate as a white solid.

후처리

  1. customThe vial was capped
  2. customirradiated in a microwave at 120° C. for 20 min
  3. temperatureto cool

출처 및 근거

ORD 기록
ord-21f2f53d71264236a25892855b40e9ac
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096527B2

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