Triethylamine → HCID 18967530, compound

HRID 235154Notes

Reaction equation

HRID 235154 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[CH:9][CH:8]=1)(=O)=O.[C:26]([C:28]1[CH:29]=[C:30]([Sn](C)(C)C)[CH:31]=[N:32][CH:33]=1)#[N:27].C(N(CC)CC)C.[Cl-].[Li+]>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.CN(C)C=O>[C:26]([C:28]1[CH:29]=[C:30]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[C:14]3[N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:9][CH:8]=2)[CH:31]=[N:32][CH:33]=1)#[N:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 433294Lithium ChlorideHCID 186990455-(Trimethylstannyl)nicotinonitrileHCID 22115665HCID 22115665, compound

Product 1

HCID 18967530HCID 18967530, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-trifluoromethylsulfonyloxy-1-(4-methylpiperazin-1-yl)naphthalene (0.527 g, 1.53 mmol), bis(triphenylphosphine)palladium[II]chloride (0.537 g, 0.77 mmol), 5-cyano-3-trimethylstannylpyridine (0.0.450 g, 1.69 mmol, from preparation 7), triethylamine (1.02 mL, 7.34 mmol), lithium chloride (0.194 g, 4.59 mmol), 2,6-di-tert-butyl-4-methylphenol (approximately 0.01 g), and N,N-dimethylformamide (6 mL) was heated between 100° C. to 115° C. under nitrogen for 1.5 hours. The resulting mixture was concentrated via evaporation under reduced pressure, and the residue was column chromatographed using silica gel (approximately 25 g) and elution with 5% methanol in ethyl acetate to afford the title compound (0.170 g, 0.52 mmol, 34%) as a pale yellow foam: Rf =0.40 in 5% methanol in ethyl acetate; 1H (CD3OD) δ 9.08 (d, J=2.2 Hz, 1H), 8.82 (d, J=2.2 Hz, 1H), 8.43 (t, J=2.0 Hz, 1H), 8.36 (br s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.70 (dd, J=1.8 and 8.5 Hz, 1H), 7.57 (br d, J=8.2 Hz, 1H), 7.44 (t, J=7.8 Hz, 1H), 7.17 (d, J=7.3 Hz, 1H), 3.20-3.00 (br s, 4H), 2.85-2.65 (br s, 4H), 2.40 (s, 3H); LRMS (m/z, relative intensity) 328 (M+, 100); HRMS m/e calculated for C21H20N4 328.1690. Observed m/e 328.1715

Workup

  1. temperaturewas heated between 100° C. to 115° C. under nitrogen for 1.5 hours
  2. concentrationThe resulting mixture was concentrated via evaporation under reduced pressure
  3. customchromatographed
  4. washsilica gel (approximately 25 g) and elution with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-f866dd8ea6974339b90ffc5d2b46858f
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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