Sodium hydride → HCID 58266535, compound

HRID 1505982Notes

Reaction equation

HRID 1505982 reaction equation
[Br:1][C:2]1[C:7]2[C:8]3[CH:14]=[C:13]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)[CH:12]=[N:11][C:9]=3[NH:10][C:6]=2[CH:5]=[N:4][C:3]=1[C:21]#[N:22].[H-].[Na+].Cl[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C.O>[Br:1][C:2]1[C:7]2[C:8]3[CH:14]=[C:13]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)[CH:12]=[N:11][C:9]=3[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:6]=2[CH:5]=[N:4][C:3]=1[C:21]#[N:22]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 58266310HCID 58266310, compound

Product 1

HCID 58266535HCID 58266535, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (547 mg, 1.55 mmol) in DMF (25 ml) under a flow of nitrogen was added sodium hydride (93 mg, 60% dispersion in mineral oil, 2.39 mmol). After 20 min, a yellow solution had formed and (2-chloromethoxyethyl)-trimethyl-silane (358 μL, 2.02 mmol) was added. The reaction mixture was stirred at ambient temperature for 3 days, then diluted with water and sonicated. The resultant solid was collected by filtration and triturated with methanol to afford the title compound as a yellow solid (404 mg, 54%). 1H NMR (CDCl3, 300 MHz): δ 9.13 (s, 1H), 9.04 (d, J=2.2 Hz, 1H), 8.95 (d, J=2.1 Hz, 1H), 7.93-7.88 (m, 1H), 7.83-7.77 (m, 1H), 6.06 (s, 2H), 4.06 (s, 3H), 3.70-3.59 (m, 2H), 1.03-0.92 (m, 2H), −0.03 (s, 9H).

Workup

  1. customa yellow solution had formed
  2. customsonicated
  3. filtrationThe resultant solid was collected by filtration
  4. customtriturated with methanol

Sources & evidence

ORD record
ord-4afbdaacb41e406aa34b07e41d66f46e
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

Loading…