Sodium Azide → 7-[3-Fluoro-5-(4-methoxy-tetrahydro-pyran-4-yl)-phenoxymethyl]-1,2,3,9b-tetraaza-cyclopenta[a]naphthalene

HRID 2075713Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][O:13][C:14]3[CH:19]=[C:18]([C:20]4([O:26][CH3:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[C:16]([F:28])[CH:15]=3)[CH:8]=2)[N:3]=1.[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C.CCOC(C)=O.O>[F:28][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([C:20]2([O:26][CH3:27])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[CH:17]=1)[O:13][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]1[N:29]=[N:30][N:31]=[C:2]1[CH:11]=[CH:10]2

Participants

Conditions

Temperature: 130 °C

Procedure

To 9b (29 mg, 0.07 mmol) in DMF (1 mL) was added sodium azide (9 mg, 0.09 mmol). The reaction was heated at 130° C. overnight, then cooled to room temperature and diluted with EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography (50% EtOAc in hexanes) to give the desired product, 9c.

Workup

temperaturecooled to room temperature
extractionThe aqueous layer was extracted with EtOAc
dry with materialthe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by silica gel chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-e377cd0d9e4740b89695f8edfdc11941
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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