Sodium Carbonate → 2-(5-Acetyl-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocin-9-yl)-benzamide

HRID 2220208노트

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HRID 2220208 반응식
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([C:25](=[O:27])[CH3:26])[CH2:7][C:8]3[CH:15]=[CH:14][C:13](B4OC(C)(C)C(C)(C)O4)=[CH:12][C:9]=3[CH2:10][CH2:11][C:4]=2[CH:3]=1.Br[C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34].C([O-])([O-])=O.[Na+].[Na+]>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>[C:25]([N:6]1[CH2:7][C:8]2[CH:15]=[CH:14][C:13]([C:31]3[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=3[C:33]([NH2:35])=[O:34])=[CH:12][C:9]=2[CH2:10][CH2:11][C:4]2[CH:3]=[C:2]([Cl:1])[CH:29]=[CH:28][C:5]1=2)(=[O:27])[CH3:26]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 776162-BromobenzamideHCID 597724571-[2-Chloro-9-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-11,12-dihydro-6H-dibenzo[b,f]azocin-5-yl]-ethanone

생성물 1

HCID 115096582-(5-Acetyl-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocin-9-yl)-benzamide수율 58%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
80 °C

실험 절차

A 2 mL conical vial was charged with Example 22B (10 mg, 0.024 mmol), 2-bromo-benzamide (7 mg, 0.036 mmol) and Pd(PPh3)4 (3 mg). The vial was evacuated and purged with argon. EtOH (0.5 mL) and toluene (0.5 mL) were added, followed by 2M aqueous Na2CO3 (0.036 mL, 0.072 mmol). The reaction was heated to 80° C. until disappearance of the starting material was noted. The reaction was cooled to room temperature and concentrated. The product was purified by reversed-phase HPLC to afford 2-(5-Acetyl-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocin-9-yl)-benzamide (5.6 mg, 58%). HPLC Rt=1.62(b) min. m/z=405 (M+H+).

후처리

  1. customThe vial was evacuated
  2. custompurged with argon
  3. additionEtOH (0.5 mL) and toluene (0.5 mL) were added
  4. temperatureThe reaction was cooled to room temperature
  5. concentrationconcentrated
  6. customThe product was purified by reversed-phase HPLC

출처 및 근거

ORD 기록
ord-4ae594f30b904ad8bb679343b36bea78
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417040B2

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