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

HRID 1662577

反応式

HRID 1662577 の反応式
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]

参加物

6

反応物 2

HCID 57705843HCID 57705843、化合物HCID 178471816HCID 178471816、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 178454872HCID 178454872、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-153a2d7b30454173abbf1696cf23e331
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

関連ノート

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