Phenacyl bromide → 5-(2-oxo-2-phenylethyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one

HRID 1046959Notes

Reaction equation

HRID 1046959 reaction equation
[N:1]1[C:11]2[NH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>CC(N(C)C)=O>[O:22]=[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][N:6]1[C:7](=[O:16])[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[NH:10][C:11]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

5

Reactant 3

HCID 6259Phenacyl bromide2×HCID 24758Sodium hydrideHCID 701695,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one

Product 1

HCID 675040295-(2-oxo-2-phenylethyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-oneYield 24.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one (5.0 g, 1 eq.) was suspended in dimethylacetamide (DMA) (50 mL). The reaction was cooled to 0° C. and sodium hydride (60% in mineral oil) (2.07 g, 2.2 eq.) was added. The reaction was warmed to room temperature and stirred until gas evolution ceased. The reaction was cooled to 0° C. and 2-bromo-1-phenylethanone (7.04 g, 1.5 eq.) was added. The reaction was stirred at room temperature before the addition of a further quantity of 2-bromo-1-phenylethanone (9 g, 2 eq.). The reaction was quenched after 2 hours at room temperature (the reaction did not proceed to completion). The reaction was poured onto 200 mL water and extracted with dichloromethane (3×75 mL). The organic extracts were combined, washed with water (2×100 mL), brine (2×100 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (0-5% methanol in dichloromethane) gave 5-(2-oxo-2-phenylethyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one (1.9 g, 24%) as a red solid. LCMS: 330 [M+H].

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. temperatureThe reaction was cooled to 0° C.
  3. customThe reaction was quenched after 2 hours at room temperature (the reaction
  4. additionThe reaction was poured onto 200 mL water
  5. extractionextracted with dichloromethane (3×75 mL)
  6. washwashed with water (2×100 mL), brine (2×100 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by column chromatography (0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e3a56f4418544242b043b6b1e70eb78f
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

Loading…