Cesium carbonate → HCID 66740288, compound

HRID 1627291Notes

Reaction equation

HRID 1627291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([SH:23])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25].CS(O[CH2:31][C:32]1[C:37]([F:38])=[CH:36][C:35]([O:39][CH2:40][CH2:41][CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])=[CH:34][C:33]=1[Cl:51])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Si:44]([O:43][CH2:42][CH2:41][CH2:40][O:39][C:35]1[CH:36]=[C:37]([F:38])[C:32]([CH2:31][S:23][C:14]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:24][CH3:25])[CH:4]=3)([CH3:10])[CH3:9])=[CH:12][N:13]=2)=[C:33]([Cl:51])[CH:34]=1)([C:47]([CH3:49])([CH3:50])[CH3:48])([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86662225HCID 86662225, compoundHCID 178490005HCID 178490005, compound

Product 1

HCID 66740288HCID 66740288, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (548 mg, 1.52 mmol) and 4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-chloro-6-fluorobenzyl methanesulfonate (681 mg, 1.60 mmol) in CH3CN (5 mL) was added Cs2CO3 (743 mg, 2.28 mmol, 1.5 eq). The reaction mixture was stirred for 2 h, filtered and evaporated in vacuo to give a residue, which was purified by flash column chromatography (EtOAc/Hex=1:4) to afford 2-(4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-chloro-6-fluorobenzylthio)-5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (756 mg, 72%). 1H NMR (400 MHz, CDCl3) δ 7.20 (s, 1H), 6.85 (dd, J=11.04, 8.48 Hz, 1H), 6.80-6.72 (m, 2H), 6.66 (dd, J=2.37, 1.50 Hz, 1H), 6.56 (dd, J=8.11, 2.19 Hz, 1H), 6.48 (ddd, J=8.41, 4.28, 2.19 Hz, 2H), 6.44 (d, J=2.45 Hz, 1H), 6.39-6.32 (m, 2H), 4.19 (d, J=1.41 Hz, 2H), 3.99 (t, J=6.19 Hz, 2H), 3.83-3.72 (m, 5H), 1.95 (dd, J=12.08, 6.05 Hz, 2H), 1.48 (s, 6H), 0.96-0.84 (m, 10H), 0.03 (t, J=4.73 Hz, 6H).

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. customto give a residue, which
  4. customwas purified by flash column chromatography (EtOAc/Hex=1:4)

Sources & evidence

ORD record
ord-16bf01b3e6c34d44aa52fd2a3b999c62
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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