Potassium Carbonate → 3-(4-Amino-2-fluorophenyl)-5-bromopyridin-2-amine

HRID 1428097ノート

反応式

HRID 1428097 の反応式
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1B1OC(C)(C)C(C)(C)O1)[NH2:14].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:14][C:13]1[CH:15]=[CH:16][C:17]([C:4]2[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[C:11]([F:10])[CH:12]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 15165082-Amino-5-bromo-3-iodopyridineHCID 447552073-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

生成物 1

HCID 867000473-(4-Amino-2-fluorophenyl)-5-bromopyridin-2-amine収率 87.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

5-Bromo-3-iodopyridin-2-amine (300 mg), 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (238 mg), tetrakis(triphenylphosphine)palladium (58 mg) and potassium carbonate (416 mg) were suspended in dioxane (5 ml) and water (0.5 ml), and the suspension was heated under reflux at 80° C. for two days. After leaving to cool, a saturated aqueous sodium bicarbonate solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [hexane:ethyl acetate=1:2 (v/v)] to give 248 mg of the title compound as a solid.

後処理

  1. customAfter leaving
  2. temperatureto cool
  3. extractionthe organic layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [hexane:ethyl acetate=1:2 (v/v)]

出典と根拠

ORDレコード
ord-9e855f16dac34369b4d194728a9c6b29
出典データセット
uspto-grants-2015_01
特許番号
US08933103B2

反応ノート

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