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Diisopropylethylamine → 5-PyriMidinecarboxaMide, N-(5-fluoro-3-Methyl-1H-indol-1-yl)-4-Methyl-2-(2-pyridinyl)-

HRID 2381900
ノート
印刷プレビュー

反応式

HRID 2381900 の反応式
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.CN(C(SC1[N+]([O-])=CC=CC=1)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:48][C:49]1[CH:50]=[C:51]2[C:55](=[CH:56][CH:57]=1)[N:54]([NH2:58])[CH:53]=[C:52]2[CH3:59]>CN(C=O)C.O.CCOC(C)=O>[F:48][C:49]1[CH:50]=[C:51]2[C:55](=[CH:56][CH:57]=1)[N:54]([NH:58][C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:5][CH:6]=1)=[O:10])[CH:53]=[C:52]2[CH3:59]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 10571248(Dimethylamino)-N,N-dimethyl((1-oxo-1lambda~5~-pyridin-2-yl)sulfanyl)methaniminium hexafluorophosphateHCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 685549575-Fluoro-3-methyl-indol-1-ylamine

生成物 1

HCID 250994745-PyriMidinecarboxaMide, N-(5-fluoro-3-Methyl-1H-indol-1-yl)-4-Methyl-2-(2-pyridinyl)-
収率 36.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (335 mg, 1.56 mmol), HOTT (638 mg, 1.72 mmol), and DIPEA) (700 μL, 4.01 mmol in DMF (6 mL) is stirred stirred at rt under N2 for 20 min. 5-Fluoro-3-methyl-indol-1-ylamine (241 mg, 1.47 mmol) is added. The resulting mixture is stirred at rt overnight. The mixture is portioned between EtOAc and water. The organic phase is separated, washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 60% EtOAc in heptane to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)amide (193 mg, 36%) as a solid. MS: 362 (M+H). 1H NMR (300 MHz, CDCl3): δ 10.41 (s, 1H), 8.84 (s, 1H), 8.55 (s, 1H), 8.48-8.45 (m, 1H), 7.86 (t, 1H), 7.40-7.36 (m, 1H), 7.24-7.20 (m, 2H), 7.05-7.01 (m, 2H), 2.82 (s, 3H), 2.32 (s, 3H).

後処理

  1. stirringThe resulting mixture is stirred at rt overnight
  2. customThe organic phase is separated
  3. washwashed with saturated aqueous NaHCO3, water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 60% EtOAc in heptane

出典と根拠

ORDレコード
ord-4934fb47d00b4c6a8ce2c2be5681aa00
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08258130B2

反応ノート

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