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Sodium Carbonate → (1S)-1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]-3-methylphenyl}sulfonyl)phenyl]ethanol

HRID 2376989
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HRID 2376989 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C@@H:17]([OH:19])[CH3:18])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:20].[F:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1>[F:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:2]2[CH:7]=[CH:6][C:5]([S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C@@H:17]([OH:19])[CH3:18])(=[O:10])=[O:9])=[CH:4][C:3]=2[CH3:20])=[CH:24][CH:23]=1
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6

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HCID 10340Sodium CarbonateHCID 5706776trans-2-(4-Fluorophenyl)vinylboronic acidHCID 68533488(1S)-1-[2-({4-bromo-3-methylphenyl}sulfonyl)phenyl]ethanol

생성물 1

HCID 11589331(1S)-1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]-3-methylphenyl}sulfonyl)phenyl]ethanol수율 56.8%

시약·촉매·용매 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 8028Tetrahydrofuran용매

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온도
150 °C

실험 절차

An Emrys microwave vial containing (1S)-1-[2-({4-bromo-3-methylphenyl}sulfonyl)phenyl]ethanol (71 mg, 0.2 mmol), [(E)-2-(4-fluorophenyl)vinyl]boronic acid (43 mg, 0.26 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.020 mmol), THF (2 mL) and 2M aqueous sodium carbonate (1 mL) was heated in an Emrys microwave reactor at 150° C. for 10 minutes. On cooling, the mixture was partitioned between EtOAc (15 mL) and water (15 mL) and the organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica (eluant 30% EtOAc/isohexane) to afford the title compound as a white solid (45 mg). δH (500 MHz, d6 DMSO): 8.01 (1H, d, J 7.9), 7.88 (1H, d, J 8.2), 7.80 (1H, d, J 7.8), 7.73-7.63 (5H, m), 7.52 (1H, t, J 7.6), 7.37 (1H, d, J 16.3), 7.29 (1H, d, J 16.2), 7.22 (2H, t, J 8.7), 5.45 (1H, s), 5.30 (1H, s), 2.46 (3H, s), 1.11 (3H, d, J 5.9). m/z (ES+) 379 [(M-OH)+].

후처리

  1. temperatureOn cooling
  2. customthe mixture was partitioned between EtOAc (15 mL) and water (15 mL)
  3. washthe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography on silica (eluant 30% EtOAc/isohexane)

출처 및 근거

ORD 기록
ord-2b25f6e59fbc445d8e827ca525489f37
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07468393B2

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