Potassium Phosphate, Tribasic → US10023592, Example 381

HRID 518544ノート

反応式

HRID 518544 の反応式
Br[C:2]1[C:3]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[CH:4][C:5](=[O:13])[N:6]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.[CH3:19][N:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[CH:22][C:21]1=[O:35].[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:16]1([CH2:15][O:14][C:3]2[C:2]([C:24]3[CH:23]=[CH:22][C:21](=[O:35])[N:20]([CH3:19])[CH:25]=3)=[CH:7][N:6]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5](=[O:13])[CH:4]=2)[CH2:18][CH2:17]1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 454801941-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 1180219955-Bromo-4-(cyclopropylmethoxy)-1-(methylsulfonylmethyl)pyridin-2-one

生成物 1

HCID 118022007US10023592, Example 381収率 31.5%

試薬・触媒・溶媒 3

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

反応条件

温度
70 °C

実験手順

The title compound from step 4 (50 mg, 0.15 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (42 mg, 0.18 mmol), Pd(dppf)Cl2 (11 mg, 14.9 umol) and K3PO4 (63 mg, 0.3 mmol) in dioxane (5 mL) and water (5 drops) were degassed and then heated to 70° C. under N2 overnight. The reaction mixture was then concentrated under reduced pressure. The residue was purified by column chromatography (PE:DCM:EA=3:0:1 to 0:1:4) followed by preparative HPLC to afford the title compound (17.09 mg, 31.5%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 7.50 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.43 (d, J=2.4 Hz, 1H), 6.71 (d, J=9.2 Hz, 1H), 5.96 (s, 1H), 5.16 (s, 2H), 3.86 (d, J=6.8 Hz, 1H), 3.63 (s, 3H), 2.99 (s, 3H), 1.26-1.21 (m, 1H), 0.70-0.66 (m, 2H), 0.36-0.32 (m, 2H). LCMS: 365.0 (M+1)+

後処理

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue was purified by column chromatography (PE:DCM:EA=3:0:1 to 0:1:4)

出典と根拠

ORDレコード
ord-8af9d14cfcc14859a5672655846e4390
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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