Sodium hydride → HCID 117778941, compound

HRID 2206537Notes

Reaction equation

HRID 2206537 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[CH3:23])=[O:13].[H-].[Na+].Br[CH:27]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[CH3:28]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH3:28])[C:15]=1[CH3:23])=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 133890301-(1-Bromoethyl)-4-fluorobenzeneHCID 26954669HCID 26954669, compound

Product 1

HCID 117778941HCID 117778941, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1H-indole-3-carboxamide (309 mg, 1.0 mmol) was dissolved in 4 mL DMF, NaH (80 mg, 2.0 mmol) was added, the mixture was stirred at room temperature for 30 min, and then 1-(1-bromoethyl)-4-fluorobenzene (0.404 mg, 2.0 mmol) was added. The mixture was stirred at room temperature overnight and was directly purified by reverse phase HPLC (A:CH3CN, B:water+0.1% HCl. A:B=35:65 ASB C18 150*25 mm) to afford the title compound as a white solid (11 mg, yield 3%). LCMS 432 (M+H+) 1H NMR (400 MHz, CDCl3) δ 7.78 (d, J=8 Hz, 1H), 7.33 (m, 1H), 7.14 (s, 1H), 6.96 (m, 2H), 6.92 (m, 1H), 6.85-6.92 (m, 4H), 5.85 (s, 1H), 5.72 (m, 1H), 4.56 (s, 2H), 2.64 (s, 3H), 2.37 (s, 3H), 2.11 (s, 3H), 1.85 (d, J=7.2 Hz, 3H).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customwas directly purified by reverse phase HPLC (A:CH3CN, B

Sources & evidence

ORD record
ord-7a7120ceb4ac4424a7a1169b21da303b
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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