Water → 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

HRID 245865

반응식

HRID 245865 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[Sn](CCCC)(CCCC)CCCC)[CH:7]=1.Br[C:25]1[N:26]=[C:27]2[C:33]([CH:34]=[O:35])=[CH:32][N:31]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:28]2=[N:29][CH:30]=1.O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[C:25]2[N:26]=[C:27]3[C:33]([CH:34]=[O:35])=[CH:32][N:31]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:28]3=[N:29][CH:30]=2)[CH:7]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 578296122-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehydeHCID 712799216-Fluoro-1-tributylstannyl-imidazo[1,5-a]pyridine

생성물 1

HCID 866779082-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde수율 105.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

In a round-bottomed flask, 6-fluoro-1-tributylstannyl-imidazo[1,5-a]pyridine (577 mg, 0.81 mmol) and 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (210 mg, 0.59 mmol) were dissolved in DMF (5 ml). The flask was evacuated and backfilled with argon then tetrakis(triphenylphosphine)palladium (0) (33 mg, 0.029 mmol) and copper (I) iodide (22 mg, 0.12 mmol) were added. The reaction mixture was stirred at 80° C. in an oil bath for 4 h then cooled to room temperature. Water was added and the resulting suspension was filtered. The filter cake was washed with water and petroleum ether then dried under high vacuum to afford 256 mg (95%) of 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as a yellow powder.

후처리

  1. customThe flask was evacuated
  2. temperaturethen cooled to room temperature
  3. filtrationthe resulting suspension was filtered
  4. washThe filter cake was washed with water and petroleum ether
  5. customthen dried under high vacuum

출처 및 근거

ORD 기록
ord-8bb9ce7c10bf490d962e7b5c7c4af8e1
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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