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Potassium Carbonate → tert-butyl 1-(4-(8-methyl-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

HRID 1037420
ノート
印刷プレビュー

反応式

HRID 1037420 の反応式
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12.[CH3:37]B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.N#N.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>[CH3:37][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[CH2:20][CH2:21][CH2:22]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

生成物 1

HCID 67068031tert-butyl 1-(4-(8-methyl-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate収率 42%

試薬・触媒・溶媒 2

HCID 178514306
HCID 178514306、化合物
触媒
HCID 312751,4-Dioxane溶媒

実験手順

tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (50.3 mg, 0.1 mmol) was dissolved in 1,4-dioxane (5 mL). Methyl boronic acid (8.98 mg, 0.15 mmol) and potassium carbonate (41.5 mg, 0.3 mmol) were added. The solution was degassed, flushing with nitrogen tetrakis (11.56 mg, 0.01 mmol) was added and the solution was refluxed for 24 h. The reaction mixture was filtered, washed with ethyl acetate and evaporated. The crude product was purified by column chromatography using hex and ethyl acetate (0-65%) to give the title compound (20 mg, 42%). LCMS (Method I): RT=7.40 min, [M+H]+=483.

後処理

  1. customThe solution was degassed
  2. additionwas added
  3. temperaturethe solution was refluxed for 24 h
  4. filtrationThe reaction mixture was filtered
  5. washwashed with ethyl acetate
  6. customevaporated
  7. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-bc43bf3511604cc0a9417913b1be7a5d
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546376B2

反応ノート

読み込み中…

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