Sodium Azide → HCID 86645399, compound

HRID 1944053Notes

Reaction equation

HRID 1944053 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH:11]([CH3:20])[CH:12](OS(C)(=O)=O)[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:21][C:22]([O:24][CH2:25][CH2:26][CH3:27])=[O:23].[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C.CCOC(C)=O>[N:28]([CH:12]1[CH:11]([CH3:20])[N:9]2[C:10]3[C:6]([C:7]([CH2:21][C:22]([O:24][CH2:25][CH2:26][CH3:27])=[O:23])=[C:8]2[CH2:14][CH2:13]1)=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])=[N+:29]=[N-:30]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86645400HCID 86645400, compound

Product 1

HCID 86645399HCID 86645399, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Propyl {4-fluoro-6-methyl-7-[(methylsulfonyl)oxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}acetate was dissolved in DMF (1 M) and treated with NaN3 (2.0 eq.), warmed to 80° C. and stirred overnight. The reaction mixture was diluted with EtOAc and extracted with sat'd NH4Cl, water, dried (Na2SO4) and concentrated. Chromatography on SiO2 (0-100% EtOAc/hexanes) gave propyl (7-azido-4-fluoro-6-methyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate: 1H NMR (600 MHz, CDCl3) δ 7.30 (d, J=7.9 Hz, 1H), 6.96-6.99 (m, 1H), 6.80 (dd, J=12.6, 7.6 Hz, 1H), 4.87 (dd, J=13.2, 6.5 Hz, 1H), 4.10 (d, J=7.0 Hz, 1H), 4.02 (t, J=6.2 Hz, 2H), 3.61 (m, 2H), 3.01 (m, 2H), 2.10-2.20 (m, 2H), 1.57-1.63 (m, 2H), 1.43 (d, J=6.8 Hz, 3H), 0.87 (t, J=7.3 Hz, 3H); MS (EI) calc'd for C18H22FN4O2 [M+1]+345.2. found 345.1.

Workup

  1. extractionextracted with sat'd NH4Cl, water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-60ad61058ac54a85a7fd98e5b074e8b8
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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