Tetrabutylammonium Fluoride → 3-(3-Hydroxy-3-methylbut-1-ynyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1888495노트

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HRID 1888495 반응식
[OH:1][C:2]([CH3:29])([CH3:28])[C:3]#[C:4][C:5]1[CH:27]=[N:26][C:8]2[N:9](COCC[Si](C)(C)C)[C:10]3[CH:15]=[N:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=3[C:7]=2[CH:6]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:1][C:2]([CH3:29])([CH3:28])[C:3]#[C:4][C:5]1[CH:27]=[N:26][C:8]2[NH:9][C:10]3[CH:15]=[N:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=3[C:7]=2[CH:6]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 58266403HCID 58266403, 화합물

생성물 1

HCID 582665973-(3-Hydroxy-3-methylbut-1-ynyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile수율 12.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

A solution of 3-(3-hydroxy-3-methylbut-1-ynyl)-9-(2-trimethylsilanyl-ethoxymethyl)dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (254 mg, 0.624 mmol) in THF (12 mL) was treated with TBAF (3.7 mL, 12.5 mmol) and heated to 60° C. for 24 h. The reaction mixture was allowed to cool to ambient temperature and the solvent removed in vacuo. The resultant residue was dissolved in DCM, absorbed onto silica gel, and purified by flash chromatography (Biotage, 25 g, 1-100% EtOAc in hepatne). The light orange solid was further purified by preparative HPLC (5-85% MeCN in water (0.1% NH4OH) over 30 min, 35 mL/min) to afford the title compound as an off-white solid (21 mg, 12%). 1H NMR (DMSO-D6, 400 MHz): 12.99 (s, 1H), 9.04 (s, 1H), 8.93 (s, 1H), 8.86 (d, J=2.0 Hz, 1H), 8.69 (d, J=2.0 Hz, 1H), 5.53 (s, 1H), 1.55 (s, 6H). LCMS (Method D): RT=9.66 min, M+H+=277.

후처리

  1. temperatureto cool to ambient temperature
  2. customthe solvent removed in vacuo
  3. dissolutionThe resultant residue was dissolved in DCM
  4. customabsorbed onto silica gel
  5. custompurified by flash chromatography (Biotage, 25 g, 1-100% EtOAc in hepatne)
  6. customThe light orange solid was further purified by preparative HPLC (5-85% MeCN in water (0.1% NH4OH) over 30 min, 35 mL/min)

출처 및 근거

ORD 기록
ord-9c6ccb7c5098449292c8d8afc1ca7cc0
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501765B2

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