Methyl morpholine oxide → 3-Hydroxy-9-(2-trimethylsilanylethoxymethyl)-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1888377노트

반응식

HRID 1888377 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:31]=[N:30][C:12]3[N:13]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:14]4[CH:19]=[N:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=4[C:11]=3[CH:10]=2)O1.C[N+]1([O-])CC[O:37]CC1>C1COCC1>[OH:37][C:9]1[CH:31]=[N:30][C:12]2[N:13]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[C:14]3[CH:19]=[N:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=3[C:11]=2[CH:10]=1

참가 물질

4

반응물 2

HCID 82029Methyl morpholine oxideHCID 582666493-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9-(2-trimethylsilanylethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

생성물 1

HCID 582663213-Hydroxy-9-(2-trimethylsilanylethoxymethyl)-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile수율 97.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9-(2-trimethylsilanylethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (245 mg, 0.54 mmol) in THF (2.0 mL), under an inert atmosphere, was added N-methylmorpholine-N-oxide (191 mg, 1.63 mmol) and the reaction mixture was heated under reflux for 90 minutes. The reaction mixture was allowed to cool to ambient temperature and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, 12 g column, ISCO 0-50% ethyl acetate in cyclohexane) to afford the title compound as a white solid (180 mg, 97%). 1H NMR (CD3OD, 300 MHz): 9.10 (d, J=1.0 Hz, 1H), 8.64 (d, J=1.3 Hz, 1H), 8.35 (d, J=2.7 Hz, 1H), 8.04 (d, J=2.7 Hz, 1H), 5.99 (s, 2H), 3.59 (t, J=8.0 Hz, 2H), 0.86 (t, J=8.0 Hz, 2H), −0.14 (s, 9H). LCMS (Method B): RT=3.75 min, M+H+=341.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 90 minutes
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography (silica, 12 g column, ISCO 0-50% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-8eae5c1c398a4172b2fbcd3f25208c36
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501765B2

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