Sodium Carbonate → HCID 67980883、化合物

HRID 2406232ノート

反応式

HRID 2406232 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH2:10][N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>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.O1CCOCC1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[CH2:10][N:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 246945421-[(2-Bromophenyl)methyl]piperidin-4-one

生成物 1

HCID 67980883HCID 67980883、化合物収率 55.3%

試薬・触媒・溶媒 2

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

実験手順

To a 5 mL microwave vial equipped with a stir bar was added sodium carbonate (79 mg, 0.75 mmol). The vial was dried in an oven for 16 hours, then cooled to room temperature under nitrogen. 1-(2-Bromo-benzyl)-piperidin-4-one (100 mg, 0.37 mmol), 4-fluorophenyl boronic acid (52.2 mg, 0.37 mmol) and Pd(PPh3)4 (43 mg, 0.037 mmol) were added, followed by dioxane (5 mL) water (1 mL). The resulting mixture was degassed thoroughly with nitrogen and then heated in a microwave to 100° C. for 10 minutes. The reaction was filtered and the filtrate was concentrated. The crude residue was purified via flash chromatography (heptanes/EtOAc gradient) to afford the desired product as a yellow solid (58 mg, 40% yield). MS (ESI) ink (M+H+): 283.3.

後処理

  1. customTo a 5 mL microwave vial equipped with a stir bar
  2. customThe vial was dried in an oven for 16 hours
  3. customThe resulting mixture was degassed thoroughly with nitrogen
  4. temperatureheated in a microwave to 100° C. for 10 minutes
  5. filtrationThe reaction was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe crude residue was purified via flash chromatography (heptanes/EtOAc gradient)

出典と根拠

ORDレコード
ord-5ca16073ac8f44388a53db52f56b1ab9
出典データセット
uspto-grants-2014_08
特許番号
US08809352B2

反応ノート

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