Potassium Phosphate, Tribasic → 5-Cyclohex-1-enyl-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide

HRID 469767Notes

Reaction equation

I[C:2]1[C:3]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].[C:23]1(B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.C1COCC1>[C:23]1([C:2]2[C:3]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([CH:16]=2)[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Iodo-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide (0.05 g, 118 μmol), 2-cyclohexenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 141091-37-4, 22.1 mg, 22.9 μl, 106 mmol) and potassium phosphate (75.2 mg, 355 μmol) were combined in degassed DMF (1.1 ml)/THF (367 μl) to give a yellow solution which was heated to 80° C. and stirred for 2 days. After cooling the mixture was poured into 5 mL saturated NaHCO3 solution and extracted with i-propyl acetate (2×50 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo to give a brown oil that was purified by preparative TLC (silica gel, 2.0 mm, 1:2 n-heptane/1-propyl acetate) to give the title compound (19 mg, 42%) as light yellow solid; MS (ESI) 378.2 (M+H)+.

Workup

customto give a yellow solution which
temperatureAfter cooling the mixture
extractionextracted with i-propyl acetate (2×50 mL)
dry with materialdried with Na2SO4
concentrationconcentrated in vacuo
customto give a brown oil that
customwas purified by preparative TLC (silica gel, 2.0 mm, 1:2 n-heptane/1-propyl acetate)

Sources & evidence

ORD record: ord-0f52222b8779469787a36fb510317d03
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629166B2

Reaction notes

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