Sodium Carbonate → HCID 68813792, compound

HRID 2104988Notes

Reaction equation

HRID 2104988 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.[C:54]([O-:57])([O-])=[O:55].[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]([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)[C:4]2[N:5]([C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[C:2]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:54]([OH:57])=[O:55])[N:3]=2)[CH:45]=1)[CH3:48]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 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 68813792HCID 68813792, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
170 °C

Procedure

A suspension of 66.3 (100 mg, 0.13 mmol), 2-carboxyl phenylboronic acid (30 mg, 0.2 mmol), Na2CO3 (56 mg, 0.52 mmol) in 3:1 DME/H2O (3 mL) was degassed and then added in Pd(PPh3)4 (10 mg). The reaction mixture was heated to 170° C. for 15 mins in microwave. The reaction mixture was adjust to PH ˜4-5, then partitioned between EtOAc and sat. NaCl, the organic layer was collected and dried over (Na2SO4), filtered and concentrated to afford Intermediate 133.1. The crude material was used in the next step without further purification. LCMS (2 min grad.) RT=2.13 min, 814.3 (M+H).

Workup

  1. customwas degassed
  2. additionadded in Pd(PPh3)4 (10 mg)
  3. custompartitioned between EtOAc and sat. NaCl
  4. customthe organic layer was collected
  5. dry with materialdried over (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1322832f2f1a4b219026f3db6876d300
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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