Water → 3-[3-(7-Methylimidazo[1,2-alpha]pyridin-3-yl)phenyl]thiophene-2-carbonitrile

HRID 985505ノート

反応式

HRID 985505 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13](B4OC(C)(C)C(C)(C)O4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.Br[C:27]1[CH:31]=[CH:30][S:29][C:28]=1[C:32]#[N:33].O>COCCOC.C(=O)([O-])[O-].[Cs+].[Cs+].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>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([C:27]4[CH:31]=[CH:30][S:29][C:28]=4[C:32]#[N:33])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

参加物

7

反応物 3

HCID 962WaterHCID 27400883-Bromothiophene-2-carbonitrileHCID 114937107-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-alpha]pyridine

生成物 1

HCID 97969523-[3-(7-Methylimidazo[1,2-alpha]pyridin-3-yl)phenyl]thiophene-2-carbonitrile収率 57.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 10796Cesium carbonate溶媒

実験手順

A mixture of 7-methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-α]pyridine (350 mg, 1.0 mmol) and 3-bromo-2-cyanothiophene (200 mg, 1.0 mmol) in 1,2-dimethoxyethane (10 ml) and caesium carbonate (5 ml of a 2M solution) was degassed for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (125 mg, 0.1 mmol) was then added and the mixture heated at reflux for 20 hours, poured into water (50 ml) and extracted with ethyl acetate (2×25 ml). The combined organic phases were dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. Purification by flash chromatography eluting with 3% methanol in dichloromethane gave the title compound as a colourless oil (180 mg, 57%). Oxalate salt, white powder, m.p. 193-195° C. (Found C, 62.07; H, 3.66; N, 10.19. C19H13N3S.C2H2O4 requires C, 62.21; H, 3.73; N, 10.36). 1H NMR (360 MHz, d6-DMSO) δH 2.42 (3H, s), 6.91-6.93 (1H, m), 7.53 (1H, s), 7.68-7.82 (6H, m), 7.89 (1H, s), 8.01 (1H, s), 8.18 (1H, d, J 5), 8.63 (1H, d, J 7); m/z (ES+) 316 (M++H).

後処理

  1. customwas degassed for 15 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux for 20 hours
  4. extractionextracted with ethyl acetate (2×25 ml)
  5. dry with materialThe combined organic phases were dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography
  9. washeluting with 3% methanol in dichloromethane

出典と根拠

ORDレコード
ord-984c98e84c9440f8bed531b864184915
出典データセット
uspto-grants-2005_03
特許番号
US06872731B2

反応ノート

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