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

HRID 2381900
Notes
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Reaction equation

HRID 2381900 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4934fb47d00b4c6a8ce2c2be5681aa00
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes