Potassium Carbonate → HCID 58516004、化合物

HRID 717847ノート

反応式

HRID 717847 の反応式
Cl[C:2]1[N:11]=[C:10]([C:12]#[N:13])[C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([F:22])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:14][C:9]1[C:10]([C:12]#[N:13])=[N:11][C:2]([C:18]2[CH:17]=[C:16]([F:15])[CH:21]=[C:20]([F:22])[CH:19]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 58515970HCID 58515970、化合物

生成物 1

HCID 58516004HCID 58516004、化合物収率 94.2%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、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

A solution of methyl 2,5-dichloro-6-cyanonicotinate (2.0 g, 8.6 mmol), (3,5-difluorophenyl)boronic acid (1.5 g, 9.5 mmol) and potassium carbonate (2.6 g, 19 mmol) in water (16 mL) and 1,4-dioxane (41 mL) were bubbled with nitrogen gas (10 minutes). Bis(triphenylphosphine)palladium(II) chloride (0.67 g, 0.95 mmol) was added and the mixture was bubbled with nitrogen gas (10 minutes). The mixture was heated at 80° C. for 1 hour and diluted with ethyl acetate and water. The aqueous layer was separated and extracted again with ethyl acetate. The combined extracts were washed with water, washed with brine, dried over sodium sulfate, filtered and evaporated. Purification on silica gel using ethyl acetate in hexanes (0-50%) gave the desired compound (2.5 g, 94%). LCMS calculated for C14H8ClF2N2O2 (M+H)+: m/z=309.0. found: 308.9.

後処理

  1. customthe mixture was bubbled with nitrogen gas (10 minutes)
  2. additiondiluted with ethyl acetate and water
  3. customThe aqueous layer was separated
  4. extractionextracted again with ethyl acetate
  5. washThe combined extracts were washed with water
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customPurification on silica gel

出典と根拠

ORDレコード
ord-d5a22cbf794444edab29fcce5d1ddec3
出典データセット
uspto-grants-2015_11
特許番号
US09193721B2

反応ノート

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