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Triethylamine → 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-3-(pyridin-3-ylethynyl)pyrazolo[1,5-a]pyridine

HRID 1253463
ノート
印刷プレビュー

反応式

HRID 1253463 の反応式
I[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:8]=[C:7]([O:17][CH3:18])[C:6]=12.[C:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)#[CH:20].C(N(CC)CC)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[CH3:18][O:17][C:7]1[C:6]2[N:5]([N:4]=[CH:3][C:2]=2[C:20]#[C:19][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=2)[CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8471TriethylamineHCID 1860033-EthynylpyridineHCID 448167683-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

生成物 1

HCID 584047844-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-3-(pyridin-3-ylethynyl)pyrazolo[1,5-a]pyridine

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 6228Dimethylformamide溶媒

実験手順

3-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (20.0 mg, 0.056 mmol), 3-ethynylpyridine (17.5 mg, 0.169 mmol), tetrakis(triphenylphosphine)palladium (0) (6.5 mg, 5.7 mmol), and copper (I) iodide (6.5 mg, 0.034 mmol) were suspended in DMF (1 ml). Triethylamine (0.016 ml, 0.113 mmol) was added, the mixture was sparged with argon for 10 minutes then allowed to stir at ambient temperature. After 1 h, the reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA. The fractions containing product were combined and diluted in ethyl acetate, then washed with aqueous sodium bicarbonate and dried over sodium sulfate, filtered and concentrated to give 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-3-(pyridin-3-ylethynyl)pyrazolo[1,5-a]pyridine. 1H NMR (600 MHz, DMSO-d6) δ 8.68 (s, 1H); 8.65 (d, 1H); 8.51 (dd, 1H); 8.30 (s, 1H); 8.17 (s, 1H); 8.03 (s, 1H); 7.85-7.88 (m, 1H); 7.40-7.43 (m, 1H); 7.02 (s, 1H); 4.02 (s, 3H); 3.85 (s, 3H). LRMS (ESI) calculated for C19H16N5O [M+H]+, 330.1; found 330.0.

後処理

  1. customthe mixture was sparged with argon for 10 minutes
  2. additionthe reaction mixture was diluted in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  8. washeluting with Acetonitrile/Water+0.05% TFA
  9. additionThe fractions containing product
  10. additiondiluted in ethyl acetate
  11. washwashed with aqueous sodium bicarbonate
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

出典と根拠

ORDレコード
ord-9858569af93a4e8fbb01671c760ff833
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08455477B2

反応ノート

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