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Potassium Carbonate → benzyl 4-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-5-pyridin-4-ylpyrazol-1-yl]piperidine-1-carboxylate

HRID 1726399
ノート
印刷プレビュー

反応式

HRID 1726399 の反応式
Br[C:2]1[C:3](C2C=CN=CC=2)=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9][CH2:8]2)[CH:6]=1.[CH2:29]([O:36]/[N:37]=[C:38]1\[CH2:39][CH2:40][C:41]2[C:46]\1=[CH:45][CH:44]=[C:43](B(O)O)[CH:42]=2)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:29]([O:36]/[N:37]=[C:38]1\[CH2:39][CH2:40][C:41]2[C:46]\1=[CH:45][CH:44]=[C:43]([C:2]1[CH:3]=[N:4][N:5]([CH:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:14])[CH2:11][CH2:12]3)[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH:42]=2)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
参加物反応条件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 68923615benzyl 4-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylateHCID 87623866[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]boronic acid

生成物 1

HCID 87625891benzyl 4-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-5-pyridin-4-ylpyrazol-1-yl]piperidine-1-carboxylate収率 166.1%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To benzyl 4-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (0.32 g; Example 5, Step 1) in 10 mL acetonitrile and 3 mL water was added 0.315 g (E)-1-(benzyloxyimino)-2,3-dihydro-1H-inden-5-ylboronic acid (prepared as described in example 2, step 4) and 0.30 g potassium carbonate. The reaction mixture was purged with nitrogen and 84 mg tetrakis(triphenyphosphine)palladium(0) catalyst was added. The reaction mixture heated to 80° C. for 2 hours, filtered through celite, and the filter cake was washed with acetonitrile. The filtrate was evaporated under vacuum to yield crude product. The residue was purified by chromatography, eluting with ethyl acetate to afford 0.36 g (83% yield) product as a colorless oil. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 598.3 by positive ESI.

後処理

  1. customThe reaction mixture was purged with nitrogen and 84 mg tetrakis(triphenyphosphine)palladium(0) catalyst
  2. additionwas added
  3. filtrationfiltered through celite
  4. washthe filter cake was washed with acetonitrile
  5. customThe filtrate was evaporated under vacuum
  6. customto yield crude product
  7. customThe residue was purified by chromatography
  8. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-0993941776bf4191adb782890b2a9cdc
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07491829B2

反応ノート

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