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

HRID 1505842ノート

反応式

HRID 1505842 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dc25a95fc392465a8cda3675f2e5a29e
出典データセット
uspto-grants-2015_12
特許番号
US09216980B2

反応ノート

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