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Potassium Phosphate, Tribasic → US10023592, Example 199

HRID 518407
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HRID 518407 반응식
[CH:1]1([CH2:4][O:5][C:6]2[C:7](I)=[N:8][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][CH:11]=2)[CH2:3][CH2:2]1.[CH3:17][N:18]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:37].[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:1]1([CH2:4][O:5][C:6]2[C:7]([C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19](=[O:37])[N:18]([CH3:17])[CH:27]=3)=[N:8][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][CH:11]=2)[CH2:3][CH2:2]1
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참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 1180225163-(Cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridineHCID 1238094992-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one

생성물 1

HCID 118022410US10023592, Example 199수율 53.1%

시약·촉매·용매 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A mixture of 3-(cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridine (140.0 mg, 0.40 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (136.5 mg, 0.48 mmol), K3PO4 (252.7 mg, 1.19 mmol) and Pd(dppf)Cl2 (29.2 mg, 0.04 mmol) in dioxane (5 mL) and H2O (1 mL) was 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 (81.0 mg, 53.1%). 1H NMR (CDCl3, 400 MHz) δ 8.33 (dd, J1=8.4 Hz, J2=1.2 Hz, 1H), 8.07 (d, J=8.4 Hz, 1H), 7.83 (d, J=8.8 Hz, 1H), 7.74 (s, 1H), 7.67 (t, J=8.4 Hz, 1H), 7.55 (t, J=8.4 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 4.01 (d, J=6.8 Hz, 2H), 3.60 (s, 3H), 3.25 (s, 3H), 1.10-0.98 (m, 1H), 0.45-0.37 (m, 2H), 0.23-0.17 (m, 2H). LCMS: 385.1 (M+1)+

후처리

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

출처 및 근거

ORD 기록
ord-56d4bfec56c1441ba63c534e5a9adf0b
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115114B2

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