Sodium hydride → HCID 57753347, compound

HRID 1931021Notes

Reaction equation

[H-].[Na+].[CH:3]([O:6][C:7]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10])([CH3:5])[CH3:4].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[CH2:29]Br>CN(C=O)C>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:22]2[C:23]=1[CH2:29][N:11]([C:9]([C:8]1[CH:12]=[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:14]=[CH:15][C:7]=1[O:6][CH:3]([CH3:5])[CH3:4])=[O:10])[CH2:21]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a RT suspension of 0.61 mmol sodium hydride (50% in mineral oil) in 0.5 ml dry DMF, a solution of 0.29 mmol 2-Isopropoxy-5-methanesulfonyl-benzamide (example B20) in 1 ml dry DMF was added dropwise. After 15 minutes at RT and 15 minutes at 50° C., the reaction mixture was cooled to 0° C., and treated by a solution of 0.29 mmol 1,2-Bis-bromomethyl-3-fluoro-benzene (CAS: 62590-16-3) in 1 ml dry DMF. The reaction mixture was allowed to warm to RT and stirred for 15 minutes then cooled to 0° C., quenched with water and extracted with ethylacetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (27% yield). MS (m/e): 378.3 [M+H+], 100%)

Workup

temperatureto warm to RT
temperaturethen cooled to 0° C.
customquenched with water
extractionextracted with ethylacetate
washThe combined organic phases were washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record: ord-6a06dd179e9047b5bd221e1e98218955
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188139B2

Reaction notes

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