Ethylacetate heptane → N-tert-butyl-3-[6'-(tetrahydro-pyran-2-yloxymethyl)-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

HRID 1928483Notes

Reaction equation

HRID 1928483 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[N:3]=1.[C:26]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([Sn](CCCC)(CCCC)CCCC)[N:41]=2)[CH:35]=1)(=[O:33])=[O:32])([CH3:29])([CH3:28])[CH3:27].CCCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:26]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]2[N:41]=[C:42]([C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=4)[CH:5]=[C:4]([CH2:18][O:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][O:21]4)[N:3]=3)[CH:43]=[CH:44][CH:45]=2)[CH:35]=1)(=[O:32])=[O:33])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 21899848Ethylacetate heptaneHCID 574686982-Bromo-6-(tetrahydro-pyran-2-yloxymethyl)-4-(4-trifluoromethyl-phenyl)-pyridineHCID 60209340HCID 60209340, compound

Product 1

HCID 68692639N-tert-butyl-3-[6'-(tetrahydro-pyran-2-yloxymethyl)-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamideYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 2-bromo-6-(tetrahydro-pyran-2-yloxymethyl)-4-(4-trifluoromethyl-phenyl)-pyridine (Example A.65) (0.400 g, 0.894 mmol), N-tert-butyl-3-(6-tributylstannanyl-pyridin-2-yl)-benzenesulfonamide (Example F.6) (0.518 g, 0.894 mmol), tetrakis(triphenyl-phosphine)palladium (0.052 g, 5 mol %) in toluene (5 mL) was heated under reflux conditions for 18 h. After cooling to rt, the reaction mixture was directly subjected to silica gel column chromatography with n-heptane/ethyl acetate to give the N-tert-butyl-3-[6′-(tetrahydro-pyran-2-yloxymethyl)-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonamide (550 mg, 98%) as a light yellow oil. MS (ISP) 626.0 [(M+H)+].

Workup

  1. temperaturewas heated under reflux conditions for 18 h

Sources & evidence

ORD record
ord-b83ff9357b834da08de472b0a135551a
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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