Sodium hydride → HCID 86681209, compound

HRID 1848237Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of N-(4-bromo-2-fluoro-6-nitrophenyl)formamide (2.79 g, 10.61 mmol) from the previous step in anhydrous DMF (40 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 485 mg, 12.13 mmol). The mixture was stirred at 0° C. for 15 min, then allowed to warm to rt. To the reaction mixture was added a solution of 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (3.04 g, 13.24 mmol) from Step 3 of Example 3 in DMF (10 mL), and the mixture was stirred at rt for 15 h. The mixture was partitioned between water and DCM and the organic layer was separated and washed sequentially with water and brine. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure to afford N-(4-bromo-2-fluoro-6-nitrophenyl)-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)formamide (4.8 g, 98%) as an oil, which was not purified further. LCMS (ESI) m/z 456 and 458 (M+H)+.

Workup

temperatureto warm to rt
stirringthe mixture was stirred at rt for 15 h
customThe mixture was partitioned between water and DCM
customthe organic layer was separated
washwashed sequentially with water and brine
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a44c51b1f3094ce6ba1b2af2dd11c8e1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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