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Potassium Phosphate, Tribasic → US10023592, Example 291

HRID 518501
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HRID 518501 반응식
Br[C:2]1[CH:3]=[C:4]([O:10][CH:11]([F:13])[F:12])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[F:14][C:15]1[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])=[CH:20][C:19]=1B1OC(C)(C)C(C)(C)O1.[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]>[F:12][CH:11]([F:13])[O:10][C:4]1[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([C:19]2[CH:20]=[C:21]([CH2:24][S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH:22]=[CH:23][C:18]=2[O:17][C:16]2[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:15]=2[F:14])[CH:3]=1
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참가 물질

7

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HCID 62657Potassium Phosphate, TribasicHCID 1180220745-Bromo-3-(difluoromethoxy)-1-methylpyridin-2-oneHCID 1239573972-[2-(2,4-Difluorophenoxy)-5-(ethylsulfonylmethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 118022412US10023592, Example 291수율 24%

시약·촉매·용매 3

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

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온도
70 °C

실험 절차

A mixture of 5-bromo-3-(difluoromethoxy)-1-methylpyridin-2-one (50 mg, 0.20 mmol), 2-[2-(2,4-difluorophenoxy)-5-(ethylsulfonylmethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (79 mg, 0.18 mmol), Pd(dppf)Cl2 (11 mg) and K3PO4 (76 mg, 0.36 mmol) in dioxane (5 mL) and water (5 drops) was purged with nitrogen, capped, and heated to 70° C. for 8 h. After the mixture was filtered, the filtrate was concentrated in vacuo and purified by prep-HPLC to afford the title compound (21 mg, 22%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.62 (d, J=2.0 Hz, 1H) 7.54 (d, J=2.0 Hz, 1H) 7.40 (d, J=2.0 Hz, 1H) 7.29 (d, J=2.0 Hz, 1H) 7.09-6.96 (m, 3H) 6.93-6.88 (m, 1H) 6.78 (m, 1H) 4.21 (s, 2H) 3.70 (s, 3H) 2.97 (q, J=7.6 Hz, 2H) 1.43 (t, J=7.6 Hz, 3H). LCMS (M+H)+=486.

후처리

  1. customwas purged with nitrogen
  2. customcapped
  3. filtrationAfter the mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. custompurified by prep-HPLC

출처 및 근거

ORD 기록
ord-02053cf989a741f8b035277afb7efbb5
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115114B2

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