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2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 117732274, compound

HRID 1772645
Notes
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Reaction equation

HRID 1772645 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=2)[CH2:2]1.Cl[C:16]1[N:17]=[C:18]2[C:23]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:22][CH:21]=[C:20]([C:30]3[CH:31]=[CH:32][C:33]([N:36]4[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]4)=[N:34][CH:35]=3)[N:19]2[CH:49]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>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]>[O:27]1[CH2:28][CH2:29][N:24]([C:23]2[C:18]3[N:19]([CH:49]=[C:16]([N:1]4[CH2:2][CH:3]([C:5]5[CH:14]=[CH:13][C:12]6[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=6)[N:6]=5)[CH2:4]4)[N:17]=3)[C:20]([C:30]3[CH:31]=[CH:32][C:33]([N:36]4[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:46])[CH3:47])=[O:43])[CH2:38][CH2:37]4)=[N:34][CH:35]=3)=[CH:21][N:22]=2)[CH2:25][CH2:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 585484432-(Azetidin-3-yl)quinolineHCID 131734675HCID 131734675, compound

Product 1

HCID 117732274HCID 117732274, compound

Reagents, catalysts & solvents 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst

Conditions

Temperature
120 °C

Procedure

A microwave vial was charged with compound 24d (154 mg, 0.840 mmol), compound 24c (350 mg, 0.700 mmol), sodium tert-butoxide (94.1 mg, 0.980 mmol), Pd2(dba)3 (12.8 mg, 0.0140 mmol), and 2-(dicyclohexylphosphino)-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (26.6 mg, 0.0560 mmol) and purged with Argon gas. Toluene (3 mL) was then added and the resulting mixture was heated in a microwave at 120° C. for 1 h. The reaction mixture was allowed to cool to rt, diluted with water (20 mL) and EtOAc (20 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated. The residue obtained was purified by flash column chromatography on silica gel (1:0-1:4 heptane/EtOAc) to obtain compound 24e. Mass Spectrum (LCMS, ESI pos.) Calcd. for C36H41N9O3: 648.3 (M+H). Found 648.4.

Workup

  1. custompurged with Argon gas
  2. additionToluene (3 mL) was then added
  3. temperatureto cool to rt
  4. additiondiluted with water (20 mL) and EtOAc (20 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customwas purified by flash column chromatography on silica gel (1:0-1:4 heptane/EtOAc)

Sources & evidence

ORD record
ord-21dccb077e2948d5be5e15d6bfd1e3d1
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249163B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes