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Dimethyloxostannane → HCID 178439146, compound

HRID 1297603
Notes
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Reaction equation

HRID 1297603 reaction equation
[C:1]([C:3]([CH3:30])([CH3:29])[C:4]1[CH:27]=[CH:26][C:7]([CH2:8][NH:9][C:10](=[O:25])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:6]([F:28])[CH:5]=1)#[N:2].[N:31]([Si](C)(C)C)=[N+:32]=[N-:33].C[Sn](=O)C>C1(C)C=CC=CC=1>[F:28][C:6]1[CH:5]=[C:4]([C:3]([CH3:30])([C:1]2[NH:33][N:32]=[N:31][N:2]=2)[CH3:29])[CH:27]=[CH:26][C:7]=1[CH2:8][NH:9][C:10](=[O:25])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 75277DimethyloxostannaneHCID 78378AzidotrimethylsilaneHCID 17832827N-[4-(Cyano-dimethyl-methyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide

Product 1

HCID 178439146HCID 178439146, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To N-[4-(cyano-dimethyl-methyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide (2.36 g) in a 50 mL sealable tube were added anhydrous toluene (2 mL), azidotrimethylsilane (1.42 mL), and dimethyl tin oxide (0.19 g). The reaction was stirred at 100° C. for seven days. The solvent was removed in vacuo. The residue was then taken up in acetone, and the precipitate was filtered and rinsed with water, giving a brown solid (1.13 g). The filtrate was concentrated, then taken up in satd. aq. sodium bicarbonate, (50 mL) and washed with ethyl acetate (50 mL). The aqueous was acidified to pH 3, and extracted with ethyl acetate (3×100 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The combined recovered solids were recrystallized with ethanol, yielding the title compound (1.26 g).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationthe precipitate was filtered
  3. washrinsed with water

Sources & evidence

ORD record
ord-577cf779f58d43839084f99b4bbe5267
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07250518B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes