Sodium Carbonate → (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

HRID 76085Notes

Reaction equation

HRID 76085 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)=[O:7])=[CH:4][N:3]=1.[CH3:21][O:22][C:23](=[O:46])[CH2:24][CH:25]1[CH2:30][CH2:29][CH:28]([C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:21][O:22][C:23](=[O:46])[CH2:24][CH:25]1[CH2:26][CH2:27][CH:28]([C:31]2[CH:32]=[CH:33][C:34]([C:2]3[CH:20]=[CH:19][C:5]([C:6](=[O:7])[NH:8][C:9]4[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=4)=[CH:4][N:3]=3)=[CH:35][CH:36]=2)[CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 57992171Methyl 2-(trans-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexyl)acetateHCID 82707315HCID 82707315, compound

Product 1

HCID 66615765(4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To 200 mg (1 mmol) 6-Bromo-N-(6-trifluoromethyl-pyridin-3-yl)-nicotinamide, 217 mg (1 mmol) {4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester in DME (20 mL), Dichloro[1,1′-bis(diphenylphosphino) ferrocene]palladium (II) dichloromethane adduct (37 mg, 5 mol %), and saturated sodium carbonate aqueous solution (2 mL) were added and the mixture stirred at 80° C. over night under N2. Evaporated to dryness and purified by passing over small plug of silica gel (30% ethyl acetate in hexanes) to afford (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester: M+1=498.1. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.06 (s, 4H) 1.12-1.20 (m, 2H) 1.45-1.57 (m, 2H) 1.81 (d, J=8.59 Hz, 4H) 2.25 (d, J=6.57 Hz, 2H) 2.50-2.57 (m, 1H) 3.60 (s, 2H) 7.39 (d, J=8.34 Hz, 2H) 7.94 (d, J=8.84 Hz, 1H) 8.07-8.15 (m, 2H) 8.35-8.43 (m, 1H) 8.50 (d, J=8.59 Hz, 1H) 9.10 (s, 1H) 9.20 (d, J=2.02 Hz, 1H).

Workup

  1. customEvaporated to dryness
  2. custompurified

Sources & evidence

ORD record
ord-7a9dce2534544beba1c5a7384de224ea
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

Loading…