Sulfuric Acid → HCID 86723392, compound

HRID 508549Notes

Reaction equation

HRID 508549 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[C:8]([F:21])=[C:7]([NH:22]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1)C.OS(O)(=O)=O.CC#N>O>[NH2:22][C:7]1[CH:6]=[C:5]([CH:4]=[O:3])[N:10]=[C:9]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:15][CH:16]=2)[C:8]=1[F:21]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723393HCID 86723393, compound

Product 1

HCID 86723392HCID 86723392, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the procedure of Example 12, 6-(diethoxymethyl)-3-fluoro-6′-(trifluoromethyl)-N-trityl-[2,3′-bipyridin]-4-amine (1203 mg, 2 mmol), conc H2SO4 (0.5 mL), CH3CN (25 mL) and H2O (25 mL) gave 4-amino-3-fluoro-6′-(trifluoromethyl)-[2,3′-bipyridine]-6-carbaldehyde (248 mg, 0.861 mmol, 43.0%) as a white solid: mp 166-167° C.; 1H NMR (400 MHz, CDCl3) δ 9.97 (s, 1H), 9.35 (s, 1H), 8.54 (d, J=8.2 Hz, 1H), 7.84 (d, J=8.2 Hz, 1H), 7.40 (d, J=6.5 Hz, 1H), 4.67 (s, 2H); 13C NMR (101 MHz, CDCl3) δ 192.35, 149.96 (d, J=8.9 Hz), 149.50 (d, J=5.2 Hz), 149.03 (d, J=260.1 Hz), 145.2, 143.03 (d, J=12.4 Hz), 140.95, 137.48 (d, J=5.3 Hz), 133.55, 122.83, 120.25 (d, J=2.7 Hz), 108.70 (d, J=4.3 Hz); 19F NMR (376 MHz, CDCl3) δ −67.98, −142.26; HRMS-ESI (m/z) [M+H]+ calcd for C12H7F4N3O, 285.0525. found, 285.0525.

Sources & evidence

ORD record
ord-fc06646ea08e49a79c953761b9a28017
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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