Sodium Azide → Propyl (7-azido-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

HRID 570643Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of propyl {4-fluoro-7-[(methylsulfonyl)oxy]-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl}acetate (1 eq) in DMF (0.15M) at 0° C. was added sodium azide (1.2 eq). The reaction mixture was stirred at 60° C. for 6 h. The reaction was quenched by addition of water and NH4Cl, extracted with EtOAc, washed with water, brine, dried and evaporated. The residue was purified by column chromatography on silica gel eluting with EtOAc/Hexanes (0 to 50%) to give the desired material as a yellow oil.

Workup

customThe reaction was quenched by addition of water and NH4Cl
extractionextracted with EtOAc
washwashed with water, brine
customdried
customevaporated
customThe residue was purified by column chromatography on silica gel eluting with EtOAc/Hexanes (0 to 50%)

Sources & evidence

ORD record: ord-751d32c77d784f8a8344896b483c3df7
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023864B2

Reaction notes

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