Sodium Carbonate → HCID 69313869, compound

HRID 1294384Notes

Reaction equation

HRID 1294384 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([NH:21][CH2:22][CH2:23][S:24][CH3:25])=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([C@@H:33]2[CH2:35][C@H:34]2[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][S:24][CH2:23][CH2:22][NH:21][C:19]([C:10]1[C:11](=[O:18])[C:12]2[C:17](=[N:16][CH:15]=[CH:14][CH:13]=2)[N:8]([C:4]2[CH:3]=[C:2]([C:27]3[CH:32]=[CH:31][C:30]([CH:33]4[CH2:35][CH:34]4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:29][CH:28]=3)[CH:7]=[CH:6][CH:5]=2)[CH:9]=1)=[O:20]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66578655ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylateHCID 69160385HCID 69160385, compound

Product 1

HCID 69313869HCID 69313869, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of amide from step 1 (1 eq), ethyl 2-(trans)-(4-bromophenyl)cyclopropanecarboxylate from EXAMPLE 1, step 1 (1 eq), Na2CO3 (3.5 eq.; 2M in H2O), Pd(PPh3)4 (0.05 eq) in n-propanol (0.1M) was stirred at 80° C. for 3 h. The mixture was cooled to rt, quenched with brine and diluted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was triturated in ether/MeOH, isolated by filtration and washed with ether to afford the title compound as a solid.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customquenched with brine
  3. additiondiluted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated in ether/MeOH
  9. customisolated by filtration
  10. washwashed with ether

Sources & evidence

ORD record
ord-a77fa842273540f483d87696336e7022
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

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