Sodium Carbonate → N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(2-(methylthio)phenyl)-1-trityl-1H-imidazol-2-yl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

HRID 2104978Notes

Reaction equation

HRID 2104978 reaction equation
Br[C:2]1[N:3]=[C:4]([CH:26]([C:40]2[CH:45]=[C:44]([O:46][CH2:47][CH3:48])[CH:43]=[C:42]([O:49][CH:50]([CH3:52])[CH3:51])[C:41]=2[F:53])[NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[N:38]=[C:37]([CH3:39])[O:36][N:35]=3)=[CH:30][CH:29]=2)[N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.[CH3:54][S:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[CH2:47]([O:46][C:44]1[CH:43]=[C:42]([O:49][CH:50]([CH3:51])[CH3:52])[C:41]([F:53])=[C:40]([CH:26]([C:4]2[N:5]([C:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:6]=[C:2]([C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=3[S:55][CH3:54])[N:3]=2)[NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[N:38]=[C:37]([CH3:39])[O:36][N:35]=3)=[CH:30][CH:29]=2)[CH:45]=1)[CH3:48]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 68813809N-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

Product 1

HCID 68813170N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(2-(methylthio)phenyl)-1-trityl-1H-imidazol-2-yl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 66.3 (48 mg, 0.06 mmol), 2-(methylthio)phenylboronic acid (12.5 mg, 0.2 mmol), Na2CO3 (28 mg, 0.24 mmol) in 3:1 DME/H2O (2 mL) was degassed and then added in Pd(PPh3)4 (10 mg). The reaction mixture was heated to 150° C. for 5 min in microwave. The reaction mixture was then partionated between EtOAc and sat. NaCl, the organic layer was collected and dried over (Na2SO4), filtered and concentrated. The crude product of Intermediate 93.1 used as is for the next step. LCMS (4 min gradient) RT=4.87 min, 816.3 (M+H).

Workup

  1. customwas degassed
  2. additionadded in Pd(PPh3)4 (10 mg)
  3. customthe organic layer was collected
  4. dry with materialdried over (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customLCMS (4 min gradient) RT=4.87 min, 816.3 (M+H)

Sources & evidence

ORD record
ord-b6dbb9189cdc43a5a478dc9404919c74
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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