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Potassium Phosphate, Tribasic → US8598210, Table XV, 1

HRID 1797990
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HRID 1797990 반응식
[CH3:1][O:2][C:3](=[O:23])[CH2:4][NH:5][C:6]([C:8]1[C:13]([OH:14])=[CH:12][C:11](OS(C(F)(F)F)(=O)=O)=[CH:10][N:9]=1)=[O:7].[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][NH:5][C:6]([C:8]1[C:13]([OH:14])=[CH:12][C:11]([C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:24])[CH:30]=2)=[CH:10][N:9]=1)=[O:7]
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6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2734323(3-Chlorophenyl)boronic acidHCID 59030680HCID 59030680, 화합물

생성물 1

HCID 24891582US8598210, Table XV, 1수율 53%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 31275
1,4-Dioxane
용매

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온도
85 °C

실험 절차

To a degassed solution of [(3-hydroxy-5-trifluoromethane-sulfonyloxy-pyridine-2-carbonyl)-amino]-acetic acid methyl ester, 5, (0.30 g, 0.84 mmol) in 1,4-dioxane (10 mL) at room temperature under N2 is added 3-chlorophenylboronic acid (0.196 g, 1.26 mmol), Pd(dppf)Cl2 (0.068 g, 0.0084 mmol) and K3PO4 (0.195 g, 0.92 mmol). The resulting suspension is heated in a sealed tube at 85° C. for 16 hours. After this time, the mixture is cooled to room temperature and concentrated under reduced pressure. The residue is then treated with 1M HCl (1 mL) and diluted with EtOAc. The organic layer is separated, washed with H2O, saturated aqueous NaCl and concentrated under reduced pressure. The crude material is purified over silica (EtOAc:heptane 3:7). The resulting solid can be crystallized from EtOAc/heptane to afford 0.143 g (53% yield) of the desired compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.77 (1 H, s), 8.36 (1 H, t, J=5.7 Hz), 8.24 (1 H, d, J=1.8 Hz), 7.50-7.53 (1 H, m), 7.39-7.42 (2H, m), 7.34-7.37 (2 H, m), 4.20 (2 H, d, J=5.9 Hz), 3.76 (3 H, s). HPLC-MS: m/z.

후처리

  1. temperatureAfter this time, the mixture is cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is then treated with 1M HCl (1 mL)
  4. additiondiluted with EtOAc
  5. customThe organic layer is separated
  6. washwashed with H2O, saturated aqueous NaCl
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material is purified over silica (EtOAc:heptane 3:7)
  9. customThe resulting solid can be crystallized from EtOAc/heptane

출처 및 근거

ORD 기록
ord-cb136e25aef649b6b1320f318b9b5303
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08343952B2

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