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Diisopropylethylamine → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol-1-yl)-amide

HRID 2382024
Notes
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Reaction equation

HRID 2382024 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([OH:17])=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=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.[CH3:49][O:50][C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[N:56]([NH2:60])[CH:55]=[C:54]2[CH3:61]>O.CCOC(C)=O.CN(C=O)C>[CH3:49][O:50][C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[N:56]([NH:60][C:15]([C:11]1[C:12]([CH3:14])=[N:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=1)=[O:17])[CH:55]=[C:54]2[CH3:61]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 10571248(Dimethylamino)-N,N-dimethyl((1-oxo-1lambda~5~-pyridin-2-yl)sulfanyl)methaniminium hexafluorophosphateHCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidHCID 685548125-Methoxy-3-methyl-indol-1-ylamine

Product 1

HCID 59199988
2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol-1-yl)-amide
Yield 32.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A microwave vial (20 mL) is charged with 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (657 mg, 2.83 mmol), HOTT (1.16 g, 3.11 mmol), DIPEA (1.35 mL, 7.73 mmol) and DMF (6 mL). The mixture is stirred at 23° C. under N2 for 15 min. 5-Methoxy-3-methyl-indol-1-ylamine (456 mg, 2.59 mmol) is added and the vial is capped. The resulting mixture is heated in a microwave (Biotage-Initiator) at 150° C. for 6 min. 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 column chromatography eluting with 45% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol-1-yl)-amide (327 mg, 32%) as a solid. MS: 391 (M+H); 1H NMR (300 MHz, d6-DMSO): δ 11.75 (s, 1H), 9.19 (s, 1H), 8.32 (d, 1H), 8.18-8.16 (m, 1H), 7.66-7.62 (m, 1H), 7.45 (td, 1H), 7.30 (d, 1H), 7.22 (s, 1H), 7.05 (d, 1H), 6.85 (dd, 1H), 3.81 (s, 3H), 2.76 (s, 3H), 2.27 (s, 3H).

Workup

  1. customthe vial is capped
  2. temperatureThe resulting mixture is heated in a microwave (Biotage-Initiator) at 150° C. for 6 min
  3. customThe organic phase is separated
  4. washwashed with saturated aqueous NaHCO3, water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography
  9. washeluting with 45% EtOAc in heptane

Sources & evidence

ORD record
ord-517eb4b213394e8895a75a33e593d0f4
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes