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Sodium Carbonate → N-(3-(2-Methoxybenzyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

HRID 392446
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HRID 392446 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.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.COCCOC>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 23521695N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine

생성물 1

HCID 23521678N-(3-(2-Methoxybenzyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium
촉매
HCID 80711,2-Dimethoxyethane용매

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온도
50 °C

실험 절차

The flask was charged with N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.180 g, 0.500 mmol), 2-methoxyphenylboronic acid (0.113 g, 0.75 mmol), 4.5 ml of DME, 1.5 ml of 2 M Na2CO3, and terakis(triphenylphosphine) palladium(0) (0.018 g, 0.016 mmol). After N2-flushing, the mixture was heated at 50° C. overnight. The reaction mixture was concentrated, diluted with water, and extracted with EtOAc. The organic layer was washed with brine and concentrated. The residue was chromatographed on a silica-gel column with 1:1 to 1:3 toluene/EtOAc to afford the title compound. 1H NMR:, 8.37 (d,1H,J=3.9 Hz), 8.24 (s,1H), 7.55 (d,1H,J=7.8 Hz), 6.74-7.17 (m,9H), 4.76 (s,2H), 3.80 (s,2H), 3.69 (s,2H), 2.94 (q,2H,J=7.3 Hz), 1.32 (t,3H,J=7.3 Hz). MS calcd. 396.2; MS (M+1) 397.2.

후처리

  1. customAfter N2-flushing
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica-gel column with 1:1 to 1:3 toluene/EtOAc

출처 및 근거

ORD 기록
ord-3eff67a610a14024858f68e130218ea1
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06800651B2

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