Sodium hydride → HCID 16223448, compound

HRID 559261Notes

Reaction equation

HRID 559261 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:27](=[O:28])[N:26]([CH3:29])[C:12]2[N:13]([CH3:25])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[N:21]=[N:22][NH:23][CH:24]=1)=[CH:16][CH:15]=3.[H-].[Na+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2[C:35](=CC=CC=2)[O:34][CH2:33]1.COCBr>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:27](=[O:28])[N:26]([CH3:29])[C:12]2[N:13]([CH3:25])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[N:21]=[N:22][N:23]([CH2:33][O:34][CH3:35])[CH:24]=1)=[CH:16][CH:15]=3

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 26541Dibenzo-18-crown-6HCID 83093Bromomethyl methyl etherHCID 178481369HCID 178481369, compound

Product 1

HCID 16223448HCID 16223448, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

209 mg (0.49 mmol) of compound from Example 47, 3-(2,4-dichlorophenyl)-1,9-dimethyl-6-(1H-[1,2,3]triazol-4-yl)-1,9-dihydropyrido[2,3-b]indol-2-one, are dissolved in 3 ml of DMF. 30 mg (0.74 mmol) of 60% NaH and a spatula tip of dibenzo-18-crown-6 are added. 80 μl of bromomethyl methyl ether are then added. The mixture is stirred at ambient temperature for 16 hours. The reaction medium is poured into water and then extracted with EtOAc and the organic phase is dried over MgSO4, filtered and evaporated to dryness, adsorbing onto silica. Purification is carried out on a silica column, elution being carried out with a gradient of EtOAc/50% cyclohexane, then with EtOAc/40% cyclohexane and, finally, 100% EtOAc. The residue is triturated in MeOH so as to obtain a beige solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customPurification
  6. washis carried out on a silica column, elution
  7. customThe residue is triturated in MeOH so as
  8. customto obtain a beige solid

Sources & evidence

ORD record
ord-5bcbb65ac79044899a59a87a31890d9f
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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