Nitrogen → 5-ethynyl-1-methyl-1H-indole

HRID 1258423

반응식

HRID 1258423 반응식
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2.[Si]([C:16]#[CH:17])(C)(C)C.N#N>C(Cl)Cl.CCN(CC)CC.CCCCCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:16]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2)#[CH:17]

참가 물질

9

반응물 3

HCID 947Nitrogen2회HCID 66111TrimethylsilylacetyleneHCID 113228355-iodo-1-methyl-1H-indole

생성물 1

HCID 122962615-ethynyl-1-methyl-1H-indole

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6344Dichloromethane용매HCID 8058Hexane용매HCID 8471Triethylamine용매

실험 절차

5-iodo-1-methyl-1H-indole (1.5 g, 5.84 mmol) were dissolved in mixture of CH2Cl2 (10 ml) and NEt3 (5 ml) and the system was evacuated-back filled by N2 thrice. Pd(PPh3)2Cl2 (122 mg, 3% mol) and TMS-acetylene (0.858 g, 8.7 mmol) were added to it and again flushed N2 into the system. CuI (89 mg, 8% mol) was added and flushed N2 very quickly and reaction was stirred under positive pressure of N2 until reaction completed by TLC (ca. 3 hours). The reaction mixture was diluted with 10 ml of hexane and filtered through celite plug, purified by passing through small column and then suspended in MeOH (20 ml) containing 10 ml of THF. NaOH was added to reaction mixture and stirred at room temp until starting material consumed completely. The reaction mixture was concentrated to 10 ml and extracted with EtOAc from aqueous NH4Cl solution, which was purified by column chromatography; Yield (60%); 1H NMR (300 MHz, CDCl3) δ: 3.03 (s, 1H), 3.73 (s, 3H, NMe), 6.45 (d, J=3.0 Hz, 1H), 7.05 (d, J=3.0 Hz, 1H), 7.23 (d, J=9.0 Hz, 1H), 7.33 (dd, J=9.0, 1.2 Hz, 1H), 7.80 (bs, 1H).

후처리

  1. customthe system was evacuated-back
  2. additionfilled by N2 thrice
  3. customflushed N2 very quickly
  4. customreaction
  5. customcompleted by TLC (ca. 3 hours)
  6. filtrationfiltered through celite plug
  7. custompurified
  8. additioncontaining 10 ml of THF
  9. additionNaOH was added to reaction mixture
  10. customconsumed completely
  11. concentrationThe reaction mixture was concentrated to 10 ml
  12. extractionextracted with EtOAc from aqueous NH4Cl solution, which
  13. customwas purified by column chromatography
  14. customYield (60%)

출처 및 근거

ORD 기록
ord-d60b3960279d4fd8aaf5511a0e28b811
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466163B2

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