Sulfuric Acid → HCID 86723387, compound

HRID 508546Notes

Reaction equation

HRID 508546 reaction equation
[CH:1]1([CH2:4][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)[CH2:3][CH2:2]1.OS(O)(=O)=O.CC#N>O>[NH2:12][C:9]1[C:10]([F:11])=[C:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:6]=[C:7]([CH:32]=[O:33])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723388HCID 86723388, compound

Product 1

HCID 86723387HCID 86723387, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the procedure for Example 12, 2-(cyclopropylmethyl)-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine (4.34 g, 8.5 mmol), conc H2SO4 (1 mL), CH3CN (35 mL) and H2O (35 mL) gave 4-amino-6-(cyclopropylmethyl)-5-fluoropicolinaldehyde (1.48 g, 88%) as an off-white solid: mp 99-100° C.; 1H NMR (400 MHz, CDCl3) δ 9.89 (s, 1H), 7.25 (d, J=6.7 Hz, 1H), 4.40 (br s, 2H), 2.76 (dd, J=7.0, 2.9 Hz, 2H), 1.17 (m, 1H), 0.50 (m, 2H), 0.29 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 193.10, 149.43 (d, J=15.4 Hz), 148.84 (d, J=253.6 Hz), 148.73 (d, J=5.4 Hz), 141.49 (d, J=12.6 Hz), 107.76 (d, J=3.8 Hz), 36.25 (d, J=1.8 Hz), 10.16 (d, J=1.5 Hz), 4.56; 19F NMR (376 MHz CDCl3) δ −144.19. HRMS-ESI (m/z) [M+H]+ calcd for C10H11FN2O, 194.0855. found, 194.0857.

Sources & evidence

ORD record
ord-fba8c1bd9744462f8feee76a48f2d612
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

Loading…