Sodium Carbonate → HCID 59853655, compound

HRID 2374277Notes

Reaction equation

HRID 2374277 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][C:13]=2[F:21])[CH2:8][CH2:7]1)=[O:5].[CH3:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:21][C:13]1[CH:14]=[C:15]([C:18](=[O:20])[CH3:19])[CH:16]=[CH:17][C:12]=1[N:9]1[CH2:8][CH2:7][N:6]([C:4]([C:3]2[C:2]([C:33]3[CH:34]=[CH:35][C:30]([CH3:29])=[CH:31][CH:32]=3)=[CH:25][CH:24]=[C:23]([N+:26]([O-:28])=[O:27])[CH:22]=2)=[O:5])[CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 59853713HCID 59853713, compound

Product 1

HCID 59853655HCID 59853655, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×

Procedure

In analogy to a procedure described by Leadbeater et al. [N.E. Leadbeater, M. Marco, Org. Lett. 4, 2973 (2002)] a stirred mixture of 1 eq. 1-{4-[4-(2-bromo-5-nitro-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (Example 4), 1.05 eq. 4-methylphenylboronic acid, 1 eq. tetrabutylammonium bromide. 2.5 eq. sodium carbonate and 0.01 eq Pd(OAc)2 in water (20 ml per mmol) were heated in a sealed tube to 150° C. by microwave irradiation for 1 minute. Then the reaction mixture is diluted with water, extracted with AcOEt, the pooled organic extracts dried over Na2SO4, filtered and evaporated. The crude product is purified by preparative HPLC on a YMC Combiprep ODS-AQ column with an acetonitrile/water+0.1% formic acid gradient to yield the title compound (table 2).

Workup

  1. additiona stirred mixture of 1 eq
  2. extractionextracted with AcOEt
  3. dry with materialthe pooled organic extracts dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by preparative HPLC on a YMC Combiprep ODS-AQ column with an acetonitrile/water+0.1% formic acid gradient

Sources & evidence

ORD record
ord-392a3c1f259b4d0c87219c0a2eeca389
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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