Potassium Phosphate, Tribasic → US10023592, Example 392

HRID 518549노트

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HRID 518549 반응식
[CH3:1][N:2]1[CH:7]=[C:6](B2CC(C)(C)C(C)(C)C2)[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]1=[O:21].Br[C:23]1[CH:37]=[C:36]([S:38]([CH2:41][CH3:42])(=[O:40])=[O:39])[CH:35]=[CH:34][C:24]=1[O:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33].[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:33][C:27]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=1[O:25][C:24]1[CH:34]=[CH:35][C:36]([S:38]([CH2:41][CH3:42])(=[O:40])=[O:39])=[CH:37][C:23]=1[C:6]1[CH:5]=[C:4]([C:17]([F:18])([F:19])[F:20])[C:3](=[O:21])[N:2]([CH3:1])[CH:7]=1

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 1180217871-(2-Bromo-4-ethylsulfonylphenoxy)-2,4-difluorobenzeneHCID 1317333601-Methyl-5-(3,3,4,4-tetramethylborolan-1-yl)-3-(trifluoromethyl)pyridin-2-one

생성물 1

HCID 118021884US10023592, Example 392수율 34%

시약·촉매·용매 3

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

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온도
90 °C

실험 절차

A mixture of 1-methyl-5-(3,3,4,4-tetramethylborolan-1-yl)-3-(trifluoromethyl)pyridin-2-one (100 mg, 0.33 mmol), 1-(2-bromo-4-ethylsulfonylphenoxy)-2,4-difluorobenzene (100 mg, 0.27 mmol), Pd(dppf)Cl2 (24 mg) and K3PO4 (107 mg, 0.80 mmol) in dioxane (4 mL) and water (1 mL) was purged with nitrogen, capped, and heated to 90° C. for 4 h. After the mixture was filtered through a short bed of celite, the filtrate was concentrated in vacuo and purified by prep-HPLC afford the title compound (43 mg, 34%) as a white solid. 1H NMR (CDCl3, 400 MHz) □ ppm 8.11 (s, 1H) 7.88 (s, 2H) 7.80 (m, 1H), 7.23-7.10 (m, 1H) 7.09-6.91 (m, 2H) 6.91-6.78 (m, 1H) 6.25 (s, 1H) 3.70 (s, 3H) 3.15 (q, J=7.2 Hz, 2H) 1.31 (t, J=7.2 Hz, 3H). LCMS (M+H)+=474.

후처리

  1. customwas purged with nitrogen
  2. customcapped
  3. filtrationAfter the mixture was filtered through a short bed of celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. custompurified

출처 및 근거

ORD 기록
ord-82254af2116a470a8f9dc9b8c1a4f139
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115114B2

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