Sodium Carbonate → 4-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

HRID 1408057Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:5]=[CH:4][N:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1)([O-:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:22]2[CH:21]=[C:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:19]=[CH:18][C:17]=2[N+:14]([O-:16])=[O:15])[CH:7]=1)#[CH:9]

Participants

Conditions

Temperature: 75 °C

Procedure

A degassed mixture of 2-chloro-4-((trimethylsilyl)ethynyl)pyridine 24a, boronic ester 1.1e, 4.9 mL of 2 M aqueous Na2CO3, and 12 mL of DME was treated with 45 mg of XPHOS and 11 mg of Pd(OAc)2. The mixture was stirred at 75° C. for 1.5 h. The solvent was evaporated at reduced pressure and the residue was dissolved in 100 mL of dichloromethane. The solution was washed with water and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel chromatography eluting with a 0-20% gradient of EtOAc in CH2Cl2 to give 275 mg of product. MS (ESI, m/z) 308.1 [M+H]+.

Workup

customThe solvent was evaporated at reduced pressure
dissolutionthe residue was dissolved in 100 mL of dichloromethane
washThe solution was washed with water
dry with materialdried over Na2SO4
customThe solvent was evaporated
customthe residue was purified by silica gel chromatography
washeluting with a 0-20% gradient of EtOAc in CH2Cl2

Sources & evidence

ORD record: ord-e64637a5694146099452b3d69a8dddb6
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916569B2

Reaction notes

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