Trimethylsilylacetylene → 6-((Trimethylsilyl)ethynyl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1506064노트

반응식

HRID 1506064 반응식
Br[C:2]1[N:10]=[CH:9][C:8]2[NH:7][C:6]3[N:11]=[CH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:17][CH:16]=4)=[CH:14][C:5]=3[C:4]=2[CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>O1CCOCC1.C(Cl)Cl.CO.[Cu]I.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>[CH3:37][Si:38]([C:41]#[C:42][C:2]1[N:10]=[CH:9][C:8]2[NH:7][C:6]3[N:11]=[CH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:17][CH:16]=4)=[CH:14][C:5]=3[C:4]=2[CH:3]=1)([CH3:40])[CH3:39]

참가 물질

9

반응물 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 582663876-Bromo-3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

생성물 1

HCID 582666556-((Trimethylsilyl)ethynyl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

A mixture of 6-bromo-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (170 mg, 0.40 mmol), copper(I) iodide (7.7 mg, 0.04 mmol), and N,N-diisopropylethylamine (0.21 mL, 1.2 mmol) in anhydrous 1,4-dioxane (3 mL) was degassed and flushed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (47 mg, 0.04 mmol) and (trimethylsilyl)acetylene (0.34 mL, 2.4 mmol) were added and the reaction mixture heated at 110° C. for 1 h. The cooled reaction mixture was diluted with DCM (20 mL) and methanol (2 mL) and washed with water (15 mL). The organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford a residue that was purified by flash chromotagraphy (silica, 10 g column, Biotage, 0-10% methanol in (DCM containing 1% 7M ammonia in methanol) to afford a brown residue that was taken to the next step without further purification.

후처리

  1. customwas degassed
  2. customflushed with nitrogen
  3. customThe cooled reaction mixture
  4. washwashed with water (15 mL)
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto afford a residue that
  10. customwas purified by flash chromotagraphy (silica, 10 g column, Biotage, 0-10% methanol in (DCM containing 1% 7M ammonia in methanol)
  11. customto afford a brown residue that
  12. customwas taken to the next step without further purification

출처 및 근거

ORD 기록
ord-bb882c3a1b674bfdbbf2dd4c81d7babb
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216980B2

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