Water → HCID 22861323, compound

HRID 1956306Notes

Reaction equation

HRID 1956306 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)CC)C.[Br:22][C:23]1[N:28]=[CH:27][C:26]([C:29](Br)=[O:30])=[CH:25][CH:24]=1.O>ClCCl>[Br:22][C:23]1[N:28]=[CH:27][C:26]([C:29]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 17879038HCID 17879038, compound

Product 1

HCID 22861323HCID 22861323, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 10 ml of triethylamine in 50 ml of dichloromethane under argon is added 3 g of 6-bromopyridine-3-carbonyl bromide. The mixture is stirred at room temperature for 16 hours and then poured into 100 ml of water. The organic layer is separated and washed with 2% HCl, water, saturated NaHCO3 and dried (Na2SO4), the solvent removed under vacuum and the residue chromatographed on silica gel with ethyl acetate-hexane as solvent to give the product as a solid.

Workup

  1. customThe organic layer is separated
  2. washwashed with 2% HCl, water, saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed under vacuum
  5. customthe residue chromatographed on silica gel with ethyl acetate-hexane as solvent

Sources & evidence

ORD record
ord-ce2d84e1231d4a5b9812c51f05197488
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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