Potassium Carbonate → {4-[4-(3-Methoxy-5-nitro-pyridin-2-yl)-phenyl]cyclohexyl}-acetic acid methyl ester

HRID 76057Notes

Reaction equation

Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[CH3:13][O:14][C:15](=[O:38])[CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[CH:28]=[CH:27][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>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.COCCOC>[CH3:13][O:14][C:15](=[O:38])[CH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([C:23]2[CH:24]=[CH:25][C:26]([C:2]3[C:7]([O:8][CH3:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=3)=[CH:27][CH:28]=2)[CH2:21][CH2:22]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro-3-methoxy-5-nitro-pyridine (0.10 g, 0.53 mmol, 1.0 equiv) and {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (0.2 g, 0.56 mmol, 1.05 equiv) in 5 Ml DME was added 0.5 Ml saturated potassium carbonate solution and 10 mg Pd(PPh3)4 catalyst. The reaction was heated to 100° C. for 2 h. The crude reaction mixture was then concentrated in vacuo and then loaded directly onto a silica gel column. Elution with 30% EtOAc/hexanes afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.19 (m, 2H) 1.15 (d, J=13.14 Hz, 1H) 1.46-1.59 (m, 1H) 1.51 (dd, J=112.38, 2.78 Hz, 2H) 1.81 (d, J=5.56 Hz, 4H) 2.26 (d, J=6.82 Hz, 2H) 3.61 (s, 3H) 4.00 (s, 3H) 7.36 (d, J=8.34 Hz, 2H) 7.90 (d, J=8.34 Hz, 2H) 8.20 (d, J=2.02 Hz, 1H) 9.05 (s, 1H); (M+H)+385.1.

Workup

customThe crude reaction mixture
concentrationwas then concentrated in vacuo
washElution with 30% EtOAc/hexanes

Sources & evidence

ORD record: ord-6aaddad0bc404746b90287b4b73eb41a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835451B2

Reaction notes

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