Potassium Carbonate → HCID 77230877、化合物

HRID 402845

反応式

HRID 402845 の反応式
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:14]=[O:15])=[CH:5][N:6]2[CH:11]([CH3:13])[CH3:12].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.Cl[Pd]Cl.[Fe]>[CH:16]1([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4]([CH:14]=[O:15])=[CH:5][N:6]3[CH:11]([CH3:13])[CH3:12])[CH2:18][CH2:17]1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 772308814-bromo-1-isopropyl-1H-indole-3-carbaldehyde

生成物 1

HCID 77230877HCID 77230877、化合物収率 18.5%

試薬・触媒・溶媒 3

HCID 178454869HCID 178454869、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

To a solution of 4-romo-1-(propan-2-yl)-1H-indole-3-carboxaldehyde (120 mg, 0.451 mmol) (from Example 9-1, Step 1) and cyclopropylboronic acid (77 mg, 0.902 mmol) in dioxane (2 mL) and water (0.5 mL) in a 5 mL microwave reaction vial was added potassium carbonate (187 mg, 1.35 mmol) and dichloro[1,1′-bis(di-t-butylphosphino)ferrocene]palladium (II) (29 mg, 0.045 mmol). The reaction was placed under nitrogen, sealed and heated in a microwave reactor at 140° C. for 25 minutes. The solvent was removed in vacuo and the residue was partitioned with ethyl acetate and aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes) to give the title intermediate (19 mg).

後処理

  1. customsealed
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned with ethyl acetate and aqueous sodium bicarbonate
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-c464cef29b1846db90279fe2d76f9849
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

関連ノート

読み込み中…