Potassium Phosphate, Tribasic → 5-[2-(Cyclopropylmethoxy)-5-ethylsulfonylphenyl]-3-hydroxy-1-methylpyridin-2-one

HRID 518496ノート

反応式

HRID 518496 の反応式
Br[C:2]1[CH:3]=[C:4]([OH:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH:11]1([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][C:17]=2B2OC(C)(C)C(C)(C)O2)[CH2:13][CH2:12]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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:11]1([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][C:17]=2[C:2]2[CH:3]=[C:4]([OH:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)[CH2:12][CH2:13]1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 840489365-Bromo-3-hydroxy-1-methyl-1,2-dihydropyridin-2-oneHCID 896575182-[2-(Cyclopropylmethoxy)-5-(ethylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 1180221155-[2-(Cyclopropylmethoxy)-5-ethylsulfonylphenyl]-3-hydroxy-1-methylpyridin-2-one収率 51%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a mixture of 5-bromo-3-hydroxy-1-methylpyridin-2-one (1.00 g, 4.9 mmol), 2-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.80 g, 4.9 mmol) in dioxane (30 mL) and H2O (5 mL) was added K3PO4 (3.12 g, 14.7 mmol), Pd(dppf)Cl2 (358 mg, 0.49 mmol). After purging the mixture with nitrogen, the mixture was stirred at 90° C. under microwave irridation for 1 h. After the mixture was filtered, the filtrate was concentrated to dryness. The resulting residue was purified by prep-HPLC to give the title compound (0.9 g, 51%) as a purple solid. 1H NMR (CDCl3, 400 MHz) δ 7.81 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.77 (d, J=2.4 Hz, 1H), 7.16-7.15 (m, 2H), 3.95 (d, J=6.8 Hz, 2H), 3.70 (s, 3H), 3.12 (q, J=7.6 Hz, 2H), 1.32-1.27 (m, 4H), 0.70-0.67 (m, 2H), 0.39-0.36 (m, 2H). LCMS (M+H)+=364.

後処理

  1. customAfter purging the mixture with nitrogen
  2. filtrationAfter the mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe resulting residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-1a46733cde5442fcbef593de32434b01
出典データセット
uspto-grants-2015_08
特許番号
US09115114B2

反応ノート

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