Sulfuric Acid → HCID 86723389, compound

HRID 508547Notes

Reaction equation

HRID 508547 reaction equation
[CH:1]1([C:5]2[C:10]([F:11])=[C:9]([NH:12]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:8]=[C:7]([CH:32](OCC)[O:33]CC)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.OS(O)(=O)=O.CC#N>O>[NH2:12][C:9]1[C:10]([F:11])=[C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[N:6]=[C:7]([CH:32]=[O:33])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723390HCID 86723390, compound

Product 1

HCID 86723389HCID 86723389, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the Procedure of Example 12, 2-cyclobutyl-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine (2.298 g, 4.5 mmol), conc H2SO4 (1 mL), CH3CN (35 mL) and H2O (35 mL) gave 4-amino-6-cyclobutyl-5-fluoropicolinaldehyde (0.780 g, 88%) as a white solid: mp 134-135° C.; 1H NMR (400 MHz, CDCl3) δ 9.92 (s, 1H), 7.22 (d, J=6.7 Hz, 1H), 4.34 (s, 2H), 3.90 (m, 2H), 2.51 (pd, J=9.3, 2.4 Hz, 3H), 2.32 (qt, J=8.5, 2.7 Hz, 3H), 2.03 (m, 4H); 13C NMR (101 MHz, CDCl3) δ 193.39, 151.45 (d, J=14.5 Hz), 148.62 (d, J=5.4 Hz), 148.24 (d, J=253.9 Hz), 141.03 (d, J=12.5 Hz), 107.43 (d, J=3.6 Hz), 35.38 (d, J=2.0 Hz), 27.00 (d, J=1.6 Hz), 18.64; 19F NMR (376 MHz, CDCl3) δ −144.82; HRMS-ESI (m/z) [M+H]+ calcd for C10H11FN2O, 194.0855. found, 194.0855.

Sources & evidence

ORD record
ord-df577527e506425da2d1a6e7580fed06
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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