Potassium Phosphate, Tribasic → US10023592, Example 259

HRID 575744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 575744
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]2[CH:17]=[CH:18][O:19][C:4]=2[C:3]1=[O:20].[CH:21]1([CH2:24][O:25][C:26]2[C:27](I)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:23][CH2:22]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]>[CH:21]1([CH2:24][O:25][C:26]2[C:27]([C:6]3[C:5]4[CH:17]=[CH:18][O:19][C:4]=4[C:3](=[O:20])[N:2]([CH3:1])[CH:7]=3)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:22][CH2:23]1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 1180225163-(Cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridineHCID 1240169906-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one

Produkt 1

HCID 118021483US10023592, Example 259Ausbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one (50 mg, 0.18 mmol), 3-(cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridine (53 mg, 0.15 mmol), K3PO4 (114 mg, 0.54 mmol), Pd(dppf)Cl2 (13 mg, 0.018 mmol) in dioxane (5 mL) was bubbled with nitrogen for 5 min and then stirred at 70° C. for 12 h. The reaction mixture was concentrated, treated with DCM (30 mL), washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC to give the title compound (35 mg, yield: 52%) as an off-white solid.

Aufarbeitung

  1. customwas bubbled with nitrogen for 5 min
  2. concentrationThe reaction mixture was concentrated
  3. additiontreated with DCM (30 mL)
  4. washwashed with water (30 mL) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bb88270f86ec4626a0d64e6820f4df77
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034900B2

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