Bromobenzene → HCID 68180918, compound

HRID 538677Notes

Reaction equation

HRID 538677 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH2:14][NH:15][CH:16]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:26]1[CH:31]=CC=C[CH:27]=1.CN([C:35]1[C:40](C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=C[CH:36]=1)C.CC([O-])(C)C.[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH2:14][NH:15][C:16]1[CH:17]=[CH:31][CH:26]=[CH:27][C:24]=1[CH:23]1[CH2:22][C:21]2[C:36](=[CH:35][CH:40]=[CH:19][CH:20]=2)[CH2:18]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23665647Potassium tert-butoxideHCID 68180905HCID 68180905, compound

Product 1

HCID 68180918HCID 68180918, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of compound 39 (1.5 g, 4.54 mmol) in dioxane (22 mL) were added bromobenzene (1 mL, 9.09 mmol), DavePhos (0.36 g, 0.91 mmol), and KOtBu (1.28 g, 11.36 mmol) and purged with argon for 15 minutes. Then Pd2(dba)3 (0.42 g, 0.45 mmol) was added and the solution was again purged for 15 minutes. The reaction mixture was heated in a microwave for 1 hour at 100° C. The reaction mixture was diluted in ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified by Combiflash® chromatography eluting with 5-6% of ethyl acetate-hexane to provide compound 40.

Workup

  1. custompurged with argon for 15 minutes
  2. customthe solution was again purged for 15 minutes
  3. additionThe reaction mixture was diluted in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by Combiflash® chromatography
  9. washeluting with 5-6% of ethyl acetate-hexane

Sources & evidence

ORD record
ord-28740f87f05c4f0f8b0e77df7fe1354f
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

Loading…