Diethyl Ether → (7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetyl azide

HRID 29789Notes

Reaction equation

HRID 29789 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[C:11](=[O:20])[NH:12][CH2:13][CH:14]=[C:15]([CH2:16][C:17](O)=[O:18])[C:5]2=1.C(N(CC)CC)C.C1(P([N:42]=[N+:43]=[N-:44])(C2C=CC=CC=2)=O)C=CC=CC=1.C(OCC)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[C:11](=[O:20])[NH:12][CH2:13][CH:14]=[C:15]([CH2:16][C:17]([N:42]=[N+:43]=[N-:44])=[O:18])[C:5]2=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59789203(7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid

Product 1

HCID 59789187(7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetyl azide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cold solution of (7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid (0.99 g, 3.6 mmol) and triethylamine (0.36 g, 3.6 mmol) in dry DMF (10 mL) was added in dropwise a solution of diphenylphosphoryl azide (0.99 g, 3.6 mmol), in DMF (5 mL) over a period of 2 h. After removal of the cooling bath, the mixture was stirred at room temperature for 12 h. It was poured into ice and the precipitate therefore formed was collected by vacuum filtration, which appeared to be the title compound (0.10 g). Extract the rest part of the mixture with ethyl acetate (20 mL×2). The organic layers were combined, washed with saturated aqueous NaHCO3, brine, and dried over anhydrous Na2SO4. It was concentrated and the oil obtained was treated with diethyl ether to give additional title compound as a solid precipitate (0.23 g).

Workup

  1. customAfter removal of the cooling bath
  2. additionIt was poured into ice
  3. customthe precipitate therefore formed
  4. filtrationwas collected by vacuum filtration, which
  5. extractionExtract the rest part of the mixture with ethyl acetate (20 mL×2)
  6. washwashed with saturated aqueous NaHCO3, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationIt was concentrated
  9. customthe oil obtained

Sources & evidence

ORD record
ord-3eb2d0943b404d45a89411736fa39ad2
Source dataset
uspto-grants-2008_09
Patent number
US07423031B2

Reaction notes

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