Methyl 3-(bromomethyl)benzoate → HCID 58025765, compound

HRID 1694349Notes

Reaction equation

HRID 1694349 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si](C(C)C)(C(C)C)C(C)C)[C:14]=3[O:30][CH3:31])[N:10]([C:32]([C:34]3[C:39]([F:40])=[CH:38][C:37]([F:41])=[CH:36][C:35]=3[F:42])=[O:33])[N:9]=2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:61][O:62][C:63](=[O:72])[C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([CH2:70]Br)[CH:65]=1>C(#N)C>[CH3:61][O:62][C:63](=[O:72])[C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([CH2:70][O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([CH:11]3[N:10]([C:32](=[O:33])[C:34]4[C:35]([F:42])=[CH:36][C:37]([F:41])=[CH:38][C:39]=4[F:40])[N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[S:12]3)[C:14]=2[O:30][CH3:31])[CH:65]=1

Participants

5

Reactant 3

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 2724141Tetrabutylammonium FluorideHCID 67279300HCID 67279300, compound

Product 1

HCID 58025765HCID 58025765, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[5-(4-fluoro-phenyl)-2-(2-methoxy-3-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone (0.02 mmol) is treated with tetrabutylammonium fluoride (1 M in THF) (0.04 mmol) at room temperature for 30 minutes. 3-Bromomethyl-benzoic acid methyl ester (0.04 mmol) is then added. After 30 minutes, the reaction is complete as determined by LC/MS. The mixture is diluted with acetonitrile and purified by preparative LC/MS (20-100% MeCN/H2O) to give 3-{3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxymethyl}-benzoic acid methyl ester as white solid after evaporation of solvent: 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 8.02 (d, J=7.8 Hz, 1H), 7.67 (d, J=7.7 Hz, 1H), 7.47-7.55 (m, 4H), 7.01-7.07 (m, 3H), 6.94 (t, J=8.3 Hz, 2H), 6.77 (t, J=8.5 Hz, 2H), 5.16 (s, 2H), 4.07 (s, 3H), 3.94 (s, 3H). LC/MS (ES+: (M+1) 610.9.

Workup

  1. custompurified by preparative LC/MS (20-100% MeCN/H2O)

Sources & evidence

ORD record
ord-ce0e30751cce4264830eb9f31a19cf76
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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