2-Aminobiphenyl → HCID 118006142, compound

HRID 929280Notes

Reaction equation

HRID 929280 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[C:30]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=1.[CH:43]1([C:49]2[C:54]3[O:55][C:56]4[C:61](I)=[CH:60][CH:59]=[CH:58][C:57]=4[C:53]=3[CH:52]=[CH:51][CH:50]=2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1.CC(C)([O-])C.[Na+]>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:30]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:61]1[C:56]2[O:55][C:54]3[C:49]([CH:43]4[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]4)=[CH:50][CH:51]=[CH:52][C:53]=3[C:57]=2[CH:58]=[CH:59][CH:60]=1

Participants

6

Reactant 4

HCID 70152-AminobiphenylHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 1180066684-Cyclohexyl-6-iododibenzo[b,d]furan

Product 1

HCID 118006142HCID 118006142, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Toluene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.0 g, 2.4 mmol) and Pd2(dba)3 (0.5 g, 0.6 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (3.4 g, 20.0 mmol), 4-cyclohexyl-6-iododibenzo[b,d]furan (7.5 g, 20.0 mmol), and sodium tert-butoxide (3.8 g, 40.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 24 h. After cooling, the reaction mixture was filtered through a silica pad and washed with 50% DCM/hexane. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography using 15% DCM/hexane to yield N-([1,1′-biphenyl]-2-yl)-6-cyclohexyldibenzo[b,d]furan-4-amine (8.3 g, 100% yield) as a colorless oil.

Workup

  1. customToluene (250 mL) was bubbled with nitrogen for 15 min
  2. customThe mixture was bubbled with nitrogen for 15 min
  3. customThe mixture was bubbled with nitrogen for 15 min
  4. temperaturerefluxed for 24 h
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with 50% DCM/hexane
  8. temperatureAfter cooling
  9. customthe solvent was removed in vacuo
  10. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e5facfcfa885458abf14576d62460324
Source dataset
uspto-grants-2016_03
Patent number
US09293712B2

Reaction notes

Loading…