Sodium Carbonate → 3-(3',3''-Dibenzyl-2-isobutyl-4''-methoxy-1,1':4',1''-terphenyl-4-yl)propanenitrile

HRID 971343Notes

Reaction equation

HRID 971343 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]#[N:31])=[CH:24][C:23]=2[CH2:32][CH:33]([CH3:35])[CH3:34])[CH:11]=[CH:12][C:13]=1OS(C(F)(F)F)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:36]([C:43]1[CH:44]=[C:45](B2OC(C)(C)C(C)(C)O2)[CH:46]=[CH:47][C:48]=1OC)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[C:60]([O-:63])([O-])=O.[Na+].[Na+]>COCCOC.CCO.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>[CH2:1]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]#[N:31])=[CH:24][C:23]=2[CH2:32][CH:33]([CH3:35])[CH3:34])[CH:11]=[CH:12][C:13]=1[C:47]1[CH:46]=[CH:45][C:44]([O:63][CH3:60])=[C:43]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:48]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 121347092-(3-Benzyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 12134712Trifluoro-methanesulfonic acid 3-benzyl-4'-(2-Cyano-ethyl)-2'-isobutyl-biphenyl-4-yl ester

Product 1

HCID 121347133-(3',3''-Dibenzyl-2-isobutyl-4''-methoxy-1,1':4',1''-terphenyl-4-yl)propanenitrileYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
80 °C

Procedure

167.7 mg (0.33 mmol) 4′-(2-Cyanoethyl)-3-benzyl-2′-isobutyl-1,1′-biphenyl-4-yl-trifluoromethanesulfonate (26), 158.7 mg (0.49 mmol, 1.5 eqv) 2-(3-Benzyl-4-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (23) and 58.8 mg (50.9 pmol, 0.15 eqv) Pd(Ph3P)4 were dissolved in 10 ml DME/EtOH (9+1). 0.33 ml (0.66 mmol, 2 eqv) of a 2 M aq. Na2CO3-solution was added to this yellow solution and the resulting mixture was heated at 80° C. for 8 h. After concentrating the mixture in vacuo the residue was taken up in water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (Hexanes/EtOAc (3+1)) yielded 165.6 mg (0.30 mmol, 91%) (27) as a clear oil: Rf (Hexanes/EtOAc (3+1)) 0.30; 1H NMR (500 MHz, CDCl3) δ 0.69 (d, 6H, J=6.62 Hz), 1.63 (m, 1H), 2.43 (d, 2H, J=7.41 Hz), 2.61 (t, 2H, J=7.57 Hz), 2.93 (t, 2H, J=7.57 Hz), 3.82 (s, 3H), 3.93 (s, 4H), 6.85 (d, 1H, J=8.36 Hz), 6.94 (m, 2H), 7.02-7.22 (m, 16H); LRMS (EI) m/z 549 (3), 501 (2), 446 (11), 383 (5), 335 (6), 293 (9), 256 (14), 215 (16), 214 (100), 199 (16), 160 (49), 91 (47); HRMS (EI) Calcd. for C40H39NO: 549.303164. Found: 549.302298.

Workup

  1. concentrationAfter concentrating the mixture in vacuo the residue
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-680f6ca600b24db3b3fb02e63010f411
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

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