Piperidine → 6-ethynyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 645368ノート

反応式

HRID 645368 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[N:10]=2)[CH:7]=1.C[Si]([C:24]#[CH:25])(C)C.N1CCCCC1>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-].[NH4+]>[C:24]([C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[N:10]=2)[CH:7]=1)#[CH:25]

参加物

6

反応物 3

HCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 441359396-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

生成物 1

HCID 247716676-ethynyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
25 °C

実験手順

0.2 g of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide, 156 μl of trimethylsilylacetylene, 20 mg of dichlorobis(triphenylphosphine)palladium and 2 ml of piperidine are charged to a 20 ml microwave tube. The mixture is heated for 15 minutes in the microwave device adjusted to 130° C. After cooling, the mixture is poured into 50 ml of a saturated aqueous ammonium chloride solution. Extraction is carried out twice with 70 ml of ethyl ether. The combined organic phases are separated by settling, dried and concentrated to dryness under reduced pressure. The residue is taken up in 4 ml of a 1M solution of tetrabutylammonium fluoride in THF and stirred at 25° C. for 16 hours. After evaporating the reaction medium to dryness, the residue is chromatographed on silica, elution being carried out with a mixture of cyclohexane and ethyl acetate (gradient from 0 to 35%), to give 30 mg of 6-ethynyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a beige solid.

後処理

  1. temperatureThe mixture is heated for 15 minutes in the microwave device
  2. customadjusted to 130° C
  3. temperatureAfter cooling
  4. extractionExtraction
  5. customThe combined organic phases are separated
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure
  8. customAfter evaporating the reaction medium to dryness
  9. customthe residue is chromatographed on silica, elution
  10. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (gradient from 0 to 35%)

出典と根拠

ORDレコード
ord-808a29642e3c41ac9fa5ccc320c9c30b
出典データセット
uspto-grants-2010_04
特許番号
US07704989B2

反応ノート

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