Sodium hydride → HCID 57753347, compound

HRID 225742Notes

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-ef6bd2c54b174560ba42fd45cd32d1af
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557114B2

Reaction notes

Loading…