Sulfuric Acid → HCID 86723391, compound

HRID 508548Notes

Reaction equation

HRID 508548 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:10]=[C:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([F:19])=[C:7]([NH:20]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1)C.OS(O)(=O)=O.CC#N>O>[NH2:20][C:7]1[C:8]([F:19])=[C:9]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[N:10]=[C:5]([CH:4]=[O:3])[CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723384HCID 86723384, compound

Product 1

HCID 86723391HCID 86723391, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the procedure for Example 12, 6-(diethoxymethyl)-3-fluoro-2-(4-fluorobenzyl)-N-tritylpyridin-4-amine (2.82 g, 5 mmol), conc H2SO4 (1 mL), CH3CN (35 mL) and H2O (35 mL) gave 4-amino-5-fluoro-6-(4-fluorobenzyl)picolinaldehyde (1.05 g, 83%) as a white solid: mp 130-131° C.; 1H NMR (400 MHz, CDCl3) δ 9.87 (s, 1H), 7.29 (m, 2H), 7.25 (d, J=6.7 Hz, 1H), 6.97 (m, 2H), 4.45 (s, 2H), 4.14 (d, J=3.1 Hz, 2H); 13C NMR (101 MHz, CDCl3) δ 192.85, 161.67 (d, J=244.6 Hz), 148.87 (d, J=5.4 Hz), 148.70 (d, J=254.7 Hz), 148.03 (d, J=13.7 Hz), 141.77 (d, J=12.3 Hz), 133.71 (d, J=2.7 Hz), 130.32 (d, J=8.1 Hz), 115.30 (d, J=21.3 Hz), 108.09 (d, J=3.9 Hz), 37.09; 19F NMR (376 MHz, CDCl3) δ−116.54 (m), −143.54 (dt, J=6.1, 2.7 Hz); HRMS-ESI (m/z) [M+H]+ calcd for C13H10F2N2O, 248.0761. found, 248.0763.

Sources & evidence

ORD record
ord-5333ba57c99e46f9a2d0a8c4ddb8c143
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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