2-Methoxybenzaldehyde → 3-(2-Isobutyl-4'-methoxy-3'-naphthalen-1-ylmethyl-biphenyl-4-yl)propionitrile

HRID 25840

Reaction equation

HRID 25840 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=O.COC1C=CC=CC=1C=O.C(C1C=C(C2C=CC(CCC#N)=CC=2CC(C)C)[CH:32]=[CH:33][C:34]=1[C:35]1[CH:40]=[CH:39][C:38](O)=[C:37]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH:36]=1)C1C=CC=CC=1.C(C1C=C(B2OC(C)(C)C(C)(C)O2)C=CC=1OC)C(C)C.BrC1C=CC(OC)=C(C=1)C(O)=O.[CH2:93]([C:100]1[CH:105]=[C:104](Br)C=CC=1O)[C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1.C(C1C=C(C2C=CC(CCC#N)=CC=2CC(C)C)C=CC=1C1C=CC(OCC#[N:130])=C(CC2C=CC=CC=2)C=1)C1C=CC=CC=1>>[CH2:42]([C:37]1[CH:36]=[C:35]([CH2:34][CH2:33][C:32]#[N:130])[CH:40]=[CH:39][C:38]=1[C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH2:5][C:93]2[C:94]3[C:95](=[CH:96][CH:97]=[CH:98][CH:99]=3)[CH:104]=[CH:105][CH:100]=2)[CH:8]=1)[CH:43]([CH3:44])[CH3:45]

Participants

8

Reactant 7

HCID 86582-Methoxybenzaldehyde2×HCID 113702-Methoxybenzoic acidHCID 8817395-Bromo-2-methoxybenzoic acidHCID 121347052-(3-Isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 121347153-(3',3''-Dibenzyl-4''-(cyanomethoxy)-2-isobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrileHCID 134735702-Benzyl-4-bromophenolHCID 225652293-(3'-Benzyl-4''-hydroxy-2,3''-diisobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrile

Product 1

HCID 225652733-(2-Isobutyl-4'-methoxy-3'-naphthalen-1-ylmethyl-biphenyl-4-yl)propionitrile

Procedure

452 mg (1.35 mmol) 4-(2-Cyanoethyl)-2-isobutylphenyl-trifluormethanesulfonate (6), 637.8 mg (1.70 mmol, 1.26 eq.) 2-(4-Methoxy-3-naphthalen-1-ylmethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (64) and 236.8 mg (205 μmol, 0.15 eq.) Pd(Ph3P)4 were dissolved in 20 ml DME/EtOH (9+1). To this yellow solution 1.35 ml (2.70 mmol, 2 eq.) of a 2 M aq. Na2CO3-solution was added and the resulting mixture was heated at 80° C. for 15 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 513.8 mg (1.19 mmol, 87.78%) 3-(2-Isobutyl-4′-methoxy-3′-naphthalen-1-ylm Rf (hexanes/EtOAc (3+1))=0.40. 1H-NMR (500 MHz, CDCl3): δ=0.51 (d, 6H, J=6.62 Hz, 2*CH3), 1.42 (m, 1H, CH), 2.17 (d, 2H, J=7.25 Hz, CH2), 2.56 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.87 (t, 2H, J=7.41 Hz, CH2CH2CN), 3.91 (s, 3H, OCH3), 4.42 (s, 2H, CH2Naphthyl), 6.71 (d, 1H, J=2.21 Hz), 6.94 (m, 3H), 7.00 (d, 1H, J=7.72 Hz), 7.04 (dd, 1H, J1=8.36 Hz, J2=2.36 Hz), 7.22 (m, 1H), 7.35 (m, 1H), 7.41 (m, 2H), 7.69 (d, 1H, J=8.20 Hz), 7.81 (m, 1H), 7.97 (m, 1H). MS (EI): m/z=434 (16), 433 (48), 336 (9), 335 (56), 294 (11), 293 (83), 292 (17), 277 (9), 265 (20), 264 (100), 253 (29). HR-MS (EI): Calcd. for C31H31NO: 433.240564. Found: 433.241264.

Sources & evidence

ORD record
ord-e14ed35000c54ecc9bb43e8ed425bb1d
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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