Sodium borohydride → isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate

HRID 1051094노트

반응식

HRID 1051094 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][CH2:13][C:14]3=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][CH:32]=1)[O:22][CH2:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25].[BH4-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][CH2:13][CH:14]3[NH:18][C:19]3[CH:20]=[C:21]([CH:30]=[CH:31][CH:32]=3)[O:22][CH2:23][C:24]([O:26][CH:27]([CH3:28])[CH3:29])=[O:25])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 4311764Sodium borohydrideHCID 10608474Isopropyl 2-(3-aminophenoxy)acetateHCID 820809706-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 118161547isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate수율 20.4%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
120 °C

실험 절차

Approximately forty oven dried 3 Å molecular sieves were added to a solution of 6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-one (66 mg, 0.292 mmol) and isopropyl 2-(3-aminophenoxyl)acetate (122 mg, 0.583 mmol) in toluene (3 mL) at room temperature. The reaction was heated in a 120° C. oil bath and allowed to stir overnight for approximately 16 hours. The reaction was cooled to room temperature and sodium borohydride (44 mg, 1.2 mmol) was added. The solution was stirred for 4 hours at room temperature. The reaction was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (12 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 25 mg (20%) of isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate.

후처리

  1. customApproximately forty oven dried 3 Å molecular sieves
  2. temperatureThe reaction was cooled to room temperature
  3. stirringThe solution was stirred for 4 hours at room temperature
  4. customThe reaction was quenched with saturated aqueous NaHCO3 (50 mL)
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting crude residue was purified by combiflash (12 g column, hexanes→100% ethyl acetate/hexanes, gradient)

출처 및 근거

ORD 기록
ord-a44c736568c84ba291d7837e056acb69
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388153B2

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