Potassium Phosphate, Tribasic → US10023592, Example 392

HRID 518549ノート

反応式

HRID 518549 の反応式
[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

参加物

7

反応物 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

生成物 1

HCID 118021884US10023592, Example 392収率 34%

試薬・触媒・溶媒 3

HCID 44119782Bis(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
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82254af2116a470a8f9dc9b8c1a4f139
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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