Water → 7-bromo-4-phenyl-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one

HRID 1362423Notes

Reaction equation

HRID 1362423 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][N:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:11](OCC)=[O:12])=[CH:6][C:5]([Br:22])=[CH:4][N:3]=1.[H-].[Na+].O>CS(C)=O>[Br:22][C:5]1[CH:4]=[N:3][C:2]2[NH:1][C:11](=[O:12])[CH2:10][N:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 59277611HCID 59277611, compound

Product 1

HCID 592775427-bromo-4-phenyl-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-oneYield 103%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(phenyl)amino)acetate (3.29 g, 9.0 mmol) was dissolved in anhydrous DMSO (105 mL) under Argon. NaH (361 mg of 60% dispersion in oil, 9.00 mmol) was added and the reaction was stirred for 12 h at room temperature. Water (200 mL) was added and the mixture was extracted with CH2Cl2 (4×100 mL). Combined organic layers were washed with water (200 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated to afford 7-bromo-4-phenyl-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one (2.95 g, 99%) as an orange solid: 1H NMR (300 MHz, DMSO-d6) δ 10.08 (s, 1H), 8.21 (d, J=2.4 Hz, 1H), 8.10 (d, J=2.4 Hz, 1H), 7.17-7.12 (m, 2H), 6.82-6.80 (m, 2H), 6.71-6.66 (m, 1H), 4.79 (s, 2H), 4.47 (s, 2H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (4×100 mL)
  2. washCombined organic layers were washed with water (200 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44bd3ce39c184df4a4fff6721b9c88ed
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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