Potassium Fluoride → HCID 18436712、化合物

HRID 456717

反応式

HRID 456717 の反応式
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15](I)=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][S:27][C:28]1[N:33]=[C:32]([Sn](CCCC)(CCCC)CCCC)[CH:31]=[CH:30][N:29]=1.[F-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([C:30]3[CH:31]=[CH:32][N:33]=[C:28]([S:27][CH3:26])[N:29]=3)=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 522689Potassium FluorideHCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 184367138-(Benzyloxy)-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine

生成物 1

HCID 18436712HCID 18436712、化合物収率 39%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 8-(benzyloxy)-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine (0.15 g, 0.35 mmol) and dichlorobis(triphenylphosphine)palladium(II) (30 mg, 0.0035 mmol) in toluene (3 mL) was added 2-(methylsulfanyl)-4-(tributylstannyl)pyrimidine (0.19 g, 0.46 mmol). The mixture was heated to 110° C. in a sealed tube for 16 hours. The reaction was allowed to cool and was diluted with ethyl acetate before being poured into a 10% aqueous potassium fluoride solution. The mixture was extracted with ethyl acetate. The organic phase was concentrated and the residue purified by silica chromatography, eluting with dichloromethane and then 5% acetone in dichloromethane to yield 60 mg (39%) of 8-(benzyloxy)-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)pyrimidin-4-yl]imidazo[1,2-a]pyridine. 1H NMR (CDCl3): δ 9.18 (d, 1H), 8.33 (d, 1H), 7.68 (dd, 2H), 7.54 (2H), 7.41 (m, 3H), 7.16 (t, 2H), 6.83 (m, 2H), 6.70 (d, 1H), 5.46 (s, 2H), 2.67 (s, 3H). MS m/z 443 (M+1).

後処理

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate
  3. concentrationThe organic phase was concentrated
  4. customthe residue purified by silica chromatography
  5. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-cedf43f6a5de43d19e6c6ac89c38e91c
出典データセット
uspto-grants-2007_03
特許番号
US07186714B2

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