1-Butynyltrimethylsilane → tert-Butyl 5-(but-1-yn-1-yl)-7-fluoro-1H-indole-1-carboxylate

HRID 1057136노트

반응식

HRID 1057136 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([Si](C)(C)C)#[C:20][CH2:21][CH3:22].[F:27][C:28]1[CH:29]=[C:30](I)[CH:31]=[C:32]2[C:36]=1[N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]=[CH:33]2>C(OCC)(=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>[C:19]([C:30]1[CH:31]=[C:32]2[C:36](=[C:28]([F:27])[CH:29]=1)[N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]=[CH:33]2)#[C:20][CH2:21][CH3:22]

참가 물질

7

반응물 3

HCID 439261-Butynyltrimethylsilane2회HCID 2724141Tetrabutylammonium FluorideHCID 66802356tert-Butyl 7-fluoro-5-iodo-1H-indole-1-carboxylate

생성물 1

HCID 69281207tert-Butyl 5-(but-1-yn-1-yl)-7-fluoro-1H-indole-1-carboxylate수율 91%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

To a degassed (3× vacuum/nitrogen cycles) solution of TBAF (4.0 mL, 0.5 M THF, 2.00 mmol), but-1-yn-1-yltrimethylsilane (267 mg, 2.11 mmol; Intermediate 39) was added. The solution was stirred at room temperature for a few minutes before transferring into a reaction vessel containing tert-butyl 7-fluoro-5-iodo-1H-indole-1-carboxylate (360 mg, 1.00 mmol), Pd(PPh3)4 (232 mg, 0.20 mmol), and CuI (76 mg, 0.40 mmol). The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate (100 mL), washed (50 mL water then 50 mL brine), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield the title compound as brown oil (260 mg, 91%). 1H NMR (300 MHz, DMSO-d6): δ 7.85 (d, 1H), 7.58 (d, 1H), 7.21 (dd, 1H), 6.83 (dd, 1H), 2.51 (q, 2H), 1.68 (s, 9H), 1.26 (t, 3H).

후처리

  1. additionwas added
  2. custombefore transferring into a reaction vessel
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. washwashed (50 mL water
  5. dry with material50 mL brine), dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-1c91d1820513409d9a3c5ed68b8407ed
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399646B2

반응 노트

불러오는 중…