Sodium hydride → HCID 86644969, compound

HRID 43247Notes

Reaction equation

HRID 43247 reaction equation
[H-].[Na+:2].[CH2:3]([O:6][NH:7][C:8](=[O:27])[C:9]1[C:14]([Cl:15])=[C:13]([NH2:16])[CH:12]=[C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([O:24][CH3:25])[C:18]=2[F:26])[N:10]=1)[CH:4]=[CH2:5]>C1COCC1>[CH2:3]([O:6][N-:7][C:8](=[O:27])[C:9]1[C:14]([Cl:15])=[C:13]([NH2:16])[CH:12]=[C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([O:24][CH3:25])[C:18]=2[F:26])[N:10]=1)[CH:4]=[CH2:5].[Na+:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 59471291HCID 59471291, compound

Product 1

HCID 86644969HCID 86644969, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

NaH (60% dispersion in mineral oil; 33 mg, 0.82 mmol, 1.05 equiv) was added to a stirred solution of N-(allyloxy)-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)picolinamide (300 mg, 0.78 mmol, 1.0 equiv) in THF (7.8 mL) at 23° C. The vigorously bubbling off-white mixture was stirred at 23° C. for 1 h. The resulting homogeneous light tan solution was concentrated via rotary evaporation. The residue was slurried in hexane and vacuum filtered to afford an off-white powder (260 mg, 81%): mp 236-240° C. dec; 1H NMR (300 MHz, DMSO-d6) δ 7.59 (dd, J=9, 8 Hz, 1H), 7.34 (dd, J=9, 2 Hz, 1H), 7.00 (d, J=2 Hz, 1H), 6.18 (br s, 2H), 6.01 (m, 1H), 5.18 (m, 1H), 5.03 (m, 1H), 4.13 (m, 2H), 3.92 (d, J=1 Hz, 3H).

Workup

  1. concentrationThe resulting homogeneous light tan solution was concentrated via rotary evaporation
  2. filtrationvacuum filtered

Sources & evidence

ORD record
ord-4848daa6d4114e9a90b18a64925a0222
Source dataset
uspto-grants-2013_09
Patent number
US08536331B2

Reaction notes

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