Sodium hydride → HCID 50912906, compound

HRID 2066616Notes

Reaction equation

Br[C:2]1[N:3]([CH2:10][CH:11]([OH:25])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>CN(C=O)C>[N+:7]([C:5]1[N:6]=[C:2]2[N:3]([CH:4]=1)[CH2:10][CH:11]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[O:25]2)([O-:9])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of alcohol 82 (242 mg, 0.568 mmol) in anhydrous DMF (5 mL) under N2 at 0° C. was treated with 60% NaH (36 mg, 0.90 mmol), then quickly degassed and resealed under N2. After stirring at 0° C. for 45 min, the reaction was cooled (CO2/acetone), quenched with ice/aqueous NaHCO3 (15 mL), added to brine (40 mL), and extracted with CH2Cl2 (6×50 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel, eluting with CH2Cl2, to give 1 (171 mg, 87%) as a cream solid: mp (MeOH/CH2Cl2/hexane) 170-172° C.; 1H NMR [(CD3)2SO] δ 8.16 (s, 1H), 7.31 (br dd, J=9.1, 0.8 Hz, 2H), 7.05 (dt, J=9.2, 3.1 Hz, 2H), 5.74 (m, 1H), 4.50 (dd, J=10.8, 8.9 Hz, 1H), 4.46 (dd, J=11.5, 2.8 Hz, 1H), 4.39 (dd, J=11.5, 5.2 Hz, 1H), 4.22 (dd, J=10.8, 6.5 Hz, 1H). Anal. (C13H10F3N3O5) C, H, N.

Workup

customquickly degassed
temperaturethe reaction was cooled (CO2/acetone)
customquenched with ice/aqueous NaHCO3 (15 mL)
additionadded to brine (40 mL)
extractionextracted with CH2Cl2 (6×50 mL)
customThe combined extracts were evaporated to dryness
customthe residue was chromatographed on silica gel
washeluting with CH2Cl2

Sources & evidence

ORD record: ord-93cd5b8e13e347c39016f35793232461
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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