tert-Butyl acrylate → Ethyl 6-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)imidazo[1,2-a]pyridine-3-carboxylate

HRID 1497878

반응식

HRID 1497878 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=2)[CH:7]=1.[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[CH:17]=[CH2:18].[B-](F)(F)(F)F.CC([PH+](C(C)(C)C)C(C)(C)C)(C)C.C1(CNCC2CCCCC2)CCCCC1>O1CCOCC1>[C:21]([O:20][C:16](=[O:19])[CH:17]=[CH:18][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=2)[CH:7]=1)([CH3:24])([CH3:23])[CH3:22]

참가 물질

6

반응물 4

HCID 15458tert-Butyl acrylateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 4594378Bis(cyclohexylmethyl)amineHCID 22031055Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

생성물 1

HCID 78048034Ethyl 6-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)imidazo[1,2-a]pyridine-3-carboxylate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

A stirring mixture of ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (24s) (500 mg, 1.86 mmol), tert-butyl acrylate (408 uL, 2.79 mmol), tris(dibenzylideneacetone)diplalladium(0) (51 mg, 0.056 mmol), [(t-Bu)3PH]BF4(27 mg, 0.093 mmol) and N,N-dicyclohexylmethylamine (738 uL, 3.48 mmol) in anhydrous 1,4-dioxane (5 mL) was heated at 95° C. overnight. The reaction was cooled to room temperature and filtered. The solvent was concentrated and the crude product was purified by silica chromatography to yield ethyl 6-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)imidazo[1,2-a]pyridine-3-carboxylate (70). MS m/z 317.14 (M+1)+.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe solvent was concentrated
  4. customthe crude product was purified by silica chromatography

출처 및 근거

ORD 기록
ord-17b7e77f77e54b368ff90ec2c80b18f6
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199981B2

연결된 노트

불러오는 중…