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Sodium Carbonate → 1-(3-Methylbutyl)-4-[4-(tetrahydropyran-4-ylamino)-phenyl]-1H-pyridin-2-one

HRID 1024387
ノート
印刷プレビュー

反応式

HRID 1024387 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:4](=[O:13])[CH:3]=1.[O:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH3:11][CH:10]([CH3:12])[CH2:9][CH2:8][N:5]1[CH:6]=[CH:7][C:2]([C:24]2[CH:25]=[CH:26][C:21]([NH:20][CH:17]3[CH2:16][CH2:15][O:14][CH2:19][CH2:18]3)=[CH:22][CH:23]=2)=[CH:3][C:4]1=[O:13]
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 10340Sodium CarbonateHCID 594970904-Bromo-1-isopentylpyridin-2(1H)-oneHCID 59497754(Tetrahydropyran-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine

生成物 1

HCID 594977621-(3-Methylbutyl)-4-[4-(tetrahydropyran-4-ylamino)-phenyl]-1H-pyridin-2-one収率 98.9%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

A suspension of intermediate D4 (0.46 g, 1.9 mmol), intermediate D7 (0.69 g, 2.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.21 g, 0.19 mmol) in a mixture of dioxane (4 ml) and saturated aqueous sodium carbonate (4 ml) was heated at 150° C. for 10 minutes, under microwave irradiation. The crude was filtered over diatomaceous earth and washed with EtOAc. The organic layer was separated and washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 and finally EtOAc as eluent). The desired fractions were collected and evaporated in vacuo to yield D8 (0.64 g, 95%) as a yellow solid.

後処理

  1. filtrationThe crude was filtered over diatomaceous earth
  2. washwashed with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-86e647a317b447fe85dda8e6466e5338
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722894B2

反応ノート

読み込み中…

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