Water → HCID 15380035, compound

HRID 1735024Notes

Reaction equation

HRID 1735024 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH2:17][CH2:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[H-].[Na+].O.[CH2:23](Br)[C:24]#[CH:25]>CN(C)C=O>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH2:17][CH2:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9](=[O:11])[N:10]([CH2:25][C:24]#[CH:23])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 138232839-Bromo-1,2dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one

Product 1

HCID 15380035HCID 15380035, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one (8.0 gm, 25.4 mmoles) in dimethylformamide (DMF, 120 ml) was stirred with sodium hydride (50% oil suspension, 1.9 gm, 1.6 eq) at ~0° C. (water bath) for 1.5 hours. Propargyl bromide (80% wt in toluene, 7.5 gm, 2 eq) was charged in one portion. The mixture was stirred for 30 minutes. After the starting material was consumed (TLC, dichloromethane), the solution was diluted with dichloromethane, then washed with water (3×500 ml) and brine (2×500 ml). The solution was dried over MgSO4, and concentrated on a rotary evaporator to an oil.

Workup

  1. customAfter the starting material was consumed (TLC, dichloromethane)
  2. additionthe solution was diluted with dichloromethane
  3. washwashed with water (3×500 ml) and brine (2×500 ml)
  4. dry with materialThe solution was dried over MgSO4
  5. concentrationconcentrated on a rotary evaporator to an oil

Sources & evidence

ORD record
ord-b311239c848f4c5499ba803516a1b94d
Source dataset
uspto-grants-1996_07
Patent number
US05536717

Reaction notes

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