Bromine → 3-Bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one

HRID 18249Notes

Reaction equation

HRID 18249 reaction equation
[Br:1]Br.[N:3]1[C:8]2[NH:9][C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(Cl)Cl>[Br:1][C:5]1[CH:4]=[N:3][C:8]2[NH:9][C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 124131746,7-Dihydro-5H-pyrido[2,3-b]azepin-8(9H)-one

Product 1

HCID 221390243-Bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-oneYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 10% solution of bromine (0.57 mL, 11.1 mmole) in CH2Cl2 was added dropwise over 1 hr to a solution of 5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one (1.20 g, 7.4 mmole) in CH2Cl2 at RT. The mixture was stirred at RT overnight, then was concentrated in vacuo. The residue was diluted with 10% Na2CO3 and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (EtOAc) gave the title compound (1.00 g, 56%) as a light yellow solid after drying in vacuo: MS (ES) m/e 241/243.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with 10% Na2CO3
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e34fb29c50b04a3e960599b72822fa92
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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