Sodium Carbonate → HCID 18436083, compound

HRID 351350Notes

Reaction equation

HRID 351350 reaction equation
Br[C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[CH:15]=[N:16]3)=[CH:11][C:10]=2[F:25])=[O:7])=[CH:4][CH:3]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C>[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]=[C:14]([CH2:19][N:20]5[CH2:21][CH2:22][CH2:23][CH2:24]5)[CH:15]=[N:16]4)=[CH:11][C:10]=3[F:25])=[O:7])=[CH:26][CH:27]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 18436027HCID 18436027, compound

Product 1

HCID 18436083HCID 18436083, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-N-[6-fluoro-3-(1-pyrrolidinylmethyl)-7-quinolinyl]benzamide (100 mg, 0.233 mmol) obtained in Example 49, 4-fluorophenylboronic acid (65.3 mg, 0.467 mmol) and 2N sodium carbonate (0.233 ml) in 1,2-dimethoxyethane (3 ml) was added tetrakistriphenylphosphine palladium (8.1 mg, 0.007 mmol) at 90° C., and the mixture was stirred under a nitrogen atmosphere for 16 hrs. The reaction solution was diluted with ethyl acetate and dried over anhydrous sodium sulfate. The obtained crude product was purified by NH-silica gel chromatography (eluting solvent; ethyl acetate) and treated with ethyl acetate-isopropyl ether (1:5) to give the title compound (55.2 mg) as a powder.

Workup

  1. dry with materialdried over anhydrous sodium sulfate
  2. customThe obtained crude product
  3. customwas purified by NH-silica gel chromatography (eluting solvent; ethyl acetate)
  4. additiontreated with ethyl acetate-isopropyl ether (1:5)

Sources & evidence

ORD record
ord-3270ce1301a14fa288e013cbfb320cb3
Source dataset
uspto-grants-2007_02
Patent number
US07183415B2

Reaction notes

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