HCID 57705843, 화합물 → Ethyl 3-(5-(((2-(1,1-dimethylethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-3-pyridinyl)propanoate

HRID 1662577

반응식

HRID 1662577 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=3[F:24])=[C:12]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:11]=2)[CH:7]=1.[Br-].[CH2:30]([O:32][C:33](=[O:37])[CH2:34][CH2:35][Zn+])[CH3:31]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.C1C=CC([C]2[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C]2C2C=CC=CC=2)=CC=1.[Fe].C1COCC1>[CH3:26][C:25]([C:12]1[CH:11]=[C:10]([CH2:9][O:8][C:6]2[CH:7]=[C:2]([CH2:35][CH2:34][C:33]([O:32][CH2:30][CH3:31])=[O:37])[CH:3]=[N:4][CH:5]=2)[CH:15]=[CH:14][C:13]=1[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[F:24])([CH3:28])[CH3:27]

참가 물질

6

반응물 2

HCID 57705843HCID 57705843, 화합물HCID 178471816HCID 178471816, 화합물

생성물 1

HCID 57706385Ethyl 3-(5-(((2-(1,1-dimethylethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-3-pyridinyl)propanoate수율 61%

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 178454872HCID 178454872, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a sealed tube containing 96.A (0.2020 g, 0.455 mmol), bis(dibenzylideneacetone)palladium(0) (0.0141 g, 0.0245 mmol), and CTC-Q-Phos (0.0168 g, 0.0236 mmol) was added dry THF (3 mL). After 5 minutes, 3-ethoxy-3-oxopropylzinc bromide (2.0 mL, 1.00 mmol) (0.5 M solution in THF) was added. After 1 hour, the mixture was heated to 80° C. and monitored with TLC and LC-MS. After 16.5 hours, the reaction was cooled to room temperature, and the organic solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (0-40% EtOAc/hexane) to afford 96.B which was used without further purification (129.1 mg, 61% yield). MS ESI (pos.) m/e: 466.3 (M+H)+.

후처리

  1. waitAfter 1 hour
  2. waitAfter 16.5 hours
  3. temperaturethe reaction was cooled to room temperature
  4. customthe organic solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-153a2d7b30454173abbf1696cf23e331
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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