Sulfuric Acid → HCID 86723396, compound

HRID 508551Notes

Reaction equation

HRID 508551 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:10]=[C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)[C:8]([F:16])=[C:7]([NH:17]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1)C.OS(O)(=O)=O.CC#N>O>[NH2:17][C:7]1[C:8]([F:16])=[C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)[N:10]=[C:5]([CH:4]=[O:3])[CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723397HCID 86723397, compound

Product 1

HCID 86723396HCID 86723396, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the procedure of Example 12, 6-(diethoxymethyl)-3-fluoro-2-(tetrahydrofuran-2-yl)-N-tritylpyridin-4-amine (4.21 g, 8 mmol), conc H2SO4 (1 mL), CH3CN (35 mL) and H2O (35 mL) gave 4-amino-5-fluoro-6-(tetrahydrofuran-2-yl)picolinaldehyde (1.61 g, 95%) as a white solid: mp 122-123° C.; 1H NMR (400 MHz, CDCl3) δ 9.90 (s, 1H), 7.28 (d, J=6.7 Hz, 1H), 5.26 (td, J=7.1, 1.7 Hz, 1H), 4.46 (br s, 2H), 4.17 (dt, J=7.9, 6.9 Hz, 1H), 3.98 (td, J=7.8, 5.6 Hz, 1H), 2.29 (m, 2H), 2.19 (m, 1H), 2.05 (m, 1H); 13C NMR (101 MHz, CDCl3) δ 193.12, 148.75 (d, J=5.2 Hz), 148.60 (d, J=11.7 Hz), 148.53 (d, J=256.8 Hz), 142.02 (d, J=12.1 Hz), 108.33 (d, J=4.1 Hz), 75.70, 69.26, 30.78 (d, J=0.9 Hz), 26.28; 19F NMR (376 MHz, CDCl3) δ −144.90 (d, J=6.6 Hz); HRMS-ESI (m/z) [M+H]+ calcd for C10H11FN2O2, 210.0805. found, 210.0803.

Sources & evidence

ORD record
ord-b3b03f9bd6f44f18b6cfd61c16cdc481
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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