Sodium Azide → HCID 72472700, compound

HRID 564351Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]23[CH2:26][CH2:25][CH:24]([O:27][CH2:28][CH2:29]OS(C)(=O)=O)[CH2:23][CH:12]2[CH2:13][O:14][C:15]2[C:20]3=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:35]=[N+:36]=[N-:37].[Na+]>CN(C=O)C.[NH4+].[Cl-]>[N:35]([CH2:29][CH2:28][O:27][CH:24]1[CH2:23][CH:12]2[CH2:13][O:14][C:15]3[C:20]([C:11]2([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:26][CH2:25]1)=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[F:22])=[N+:36]=[N-:37]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of methanesulfonic acid 2-[10a-(4-chloro-benzene sulfonyl)-1,4-difluoro-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-8-yloxy]-ethyl ester (180 mg, 0.355 mmol) in DMF (5 mL) was treated with NaN3 (46 mg, 0.707 mmol) and the reaction mixture was heated to 80° C. After 16 h, the reaction mixture was cooled to ambient temperature and diluted with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with H2O, saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated in vacuo to afford the title compound (153 mg, 95%): 1H NMR (CDCl3 400 MHz) δ 7.63 (d, J=8.1 Hz, 2H), 7.49 (d, J=7.3 Hz, 2H), 7.07 (m, 1H), 6.42 (m, 1H), 5.25 (dd, J=2.9, 11.7 Hz, 1H), 4.12 (d, J=11.7 Hz), 3.60 (m, 2H), 3.36 (m, 2H), 3.02 (m, 1H), 2.37 (m, 2H), 1.94 (m, 2H), 1.56 (m, 2H), 1.16 (m, 2H).

Workup

temperaturethe reaction mixture was cooled to ambient temperature
extractionextracted with EtOAc (2×)
washThe combined organic extracts were washed with H2O, saturated aqueous NaHCO3, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5ad970172976461086291c5b7d7ff5ba
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067621B2

Reaction notes

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