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Potassium Phosphate, Tribasic → US10023592, Example 190

HRID 518401
ノート
印刷プレビュー

反応式

HRID 518401 の反応式
[CH3:1][N:2]1[CH:11]=[C:10](B2OC(C)(C)C(C)(C)O2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:21].Br[C:23]1[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:26]=[CH:25][C:24]=1[NH:33][CH:34]1[CH2:38][CH2:37][O:36][CH2:35]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]>[CH3:1][N:2]1[CH:11]=[C:10]([C:23]2[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:26]=[CH:25][C:24]=2[NH:33][CH:34]2[CH2:38][CH2:37][O:36][CH2:35]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 89656503N-(2-bromo-4-methylsulfonylphenyl)oxolan-3-amineHCID 1238094992-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one

生成物 1

HCID 118021493US10023592, Example 190収率 43.9%

試薬・触媒・溶媒 3

HCID 44119782
Bis(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
70 °C

実験手順

A mixture of 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (100 mg, 0.35 mmol), the compound from Step 1 (102 mg, 0.32 mmol), K3PO4 (186 mg, 0.88 mmol) and Pd(dppf)Cl2 (29 mg, 0.04 mmol) in dioxane (5 mL) and H2O (1 mL) was purged 3 times with nitrogen and then stirred at 70° C. for 18 hrs under N2. The mixture was filtered and concentrated. The residue was purified by prep-HPLC to give the title compound (56.02 mg, yield: 40.1%) as a light yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.54 (d, J=8.0 Hz, 1H), 7.89 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.69 (s, 1H), 7.64-7.52 (m, 2H), 7.13 (s, 1H), 7.13-7.08 (m, 1H), 6.78 (dd, J1=8.8 Hz, J2=5.6 Hz, 1H), 4.17 (s, 2H), 3.94-3.86 (m, 1H), 3.79-3.72 (m, 1H), 3.72-3.64 (m, 1H), 3.67 (s, 3H), 3.58-3.49 (m, 1H), 3.07 (s, 3H), 2.32-2.18 (m, 1H), 1.76-1.63 (m, 1H). LCMS (M+H)+=399.1 (M+H)+

後処理

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-73d47a1fabf949888fa77d610b06bf24
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115114B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート