Methanol → HCID 59404395, compound

HRID 1873668Notes

Reaction equation

HRID 1873668 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][CH2:11][CH2:10][N:9]3[CH:8]=1)=[O:6])=[N+]=[N-].[O:19](C(OC(C)(C)C)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O.CO>C1COCC1.[Pd]>[C:23]([O:22][C:20](=[O:19])[NH:1][CH2:4][C:5]([C:7]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][CH2:11][CH2:10][N:9]3[CH:8]=1)=[O:6])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 90495Di-tert-butyl dicarbonateHCID 59404399HCID 59404399, compound

Product 1

HCID 59404395HCID 59404395, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-azido-1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-ethanone (4.70 g, 19.58 mmol), (BOC)2O (4.48 g, 20.56 mmol), Pd/C (10%) in THF (30 mL)/MeOH (20 mL) was shaken under H2 (60 psi) overnight. The mixture was filtered through a pad of Celite and concentrated to give a residue that was purified by silica gel column chromatography (eluent, 2/1 hex/EtOAc). [2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester was obtained as a white solid (2.82 g, 46%). M.p.=175-177° C.; 1H NMR (400 MHz, DMSO-d6) δ: 8.35 (s, 1H), 7.86 (d, J=8.0 Hz, 1H), 7.12 (t, J=7.6 Hz, 1H), 6.99 (m, 2H), 4.27 (d, J=6.0 Hz, 2H), 4.23 (t, J=6.0 Hz, 2H), 2.94 (t, J=6.4 Hz, 2H), 2.14 (m, 2H), 1.41 (s, 9H). LCMS: m/e 315.21 [M+H], 259.17 [M-56].

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customto give a residue that
  4. customwas purified by silica gel column chromatography (eluent, 2/1 hex/EtOAc)

Sources & evidence

ORD record
ord-91ccbd4777e840e9926e7d680fb6ffa8
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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