Dimethylformamide → HCID 86673617、化合物

HRID 1023470

反応式

HRID 1023470 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2OS(C(F)(F)F)(=O)=O)=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:22][C:23]1[CH:28]=[C:27]([C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:26]=[CH:25][N:24]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 51034082-Chloropyridine-4-boronic acid, pinacol esterHCID 86673616Trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester

生成物 1

HCID 86673617HCID 86673617、化合物収率 58.3%

試薬・触媒・溶媒 2

HCID 178419050HCID 178419050、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

Trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester (200 mg, 0.62 mmol), 2-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (162 mg, 0.68 mmol), Bis(triphenylphosphine)Palladium (II) dichloride (43 mg, 0.062 mmol), Sodium Carbonate solution (2.0 M, 1.54 mL, 3.1 mmol) and DMF (3 mL) are mixed in a 5 mL microwave tube with a stir bar and the mixture is heated to 100° C. in microwave reactor for 30 min. The mixture is poured to water (10 mL) and extracted with EtOAc (10 mL×3). The organic extracts are washed with water (20 mL×1), brine (20 mL×1) and dried over anhydrous sodium sulfate. After concentration, the crude is purified by silica flash column chromatography using EtOAc in Heptane (gradient from 0% to 20%) to give 104 mg of the desired product.

後処理

  1. extractionextracted with EtOAc (10 mL×3)
  2. washThe organic extracts are washed with water (20 mL×1), brine (20 mL×1)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentration
  5. customthe crude is purified by silica flash column chromatography

出典と根拠

ORDレコード
ord-f918b3db77804691a76161ae6aea9624
出典データセット
uspto-grants-2014_05
特許番号
US08722709B2

関連ノート

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