Sodium Carbonate → HCID 67980883, 화합물

HRID 2406232노트

반응식

HRID 2406232 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 67980883HCID 67980883, 화합물수율 55.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5ca16073ac8f44388a53db52f56b1ab9
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809352B2

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