Potassium Carbonate → HCID 59852896, compound

HRID 2237257Notes

Reaction equation

Cl.Cl.Cl.NCC1CN(CC#CC2C=NC=CC=2[O:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](NC(=O)CC3C=CC(F)=CC=3)=[O:28])=[CH:22][C:21]=2[F:40])C1.[Cl:41][C:42]1[CH:47]=[C:46]([N+]([O-])=O)[CH:45]=[CH:44][N:43]=1.[C:51]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:41][C:42]1[CH:47]=[C:46]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:28])[CH3:51])=[CH:22][C:21]=2[F:40])[CH:45]=[CH:44][N:43]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(3-fluoro-4-hydroxyphenyl)acetamide (Compound A of Example 13, 1.33 g, 7.87 mmol), 2-chloro-4-nitropyridine (Aldrich, 1.24 g, 7.87 mmol), K2CO3 (1.6 g, 11.8 mmol), and DMF (25 mL) was heated at 100° C. for 9 h. The mixture was concentrated in vacuo and the residue was partitioned between EtOAc and saturated aq. NaHCO3 solution. The EtOAc phase was washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash column chromatography on SiO2 eluting with 30-80% EtOAc in hexanes to give the title compound (1.6 g, 73%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 10.25 (s, 1H), 8.35 (d, 1H, J=7 Hz), 7.80 (d, 1H, J=14 Hz), 7.50 (d, 1H, J=3 Hz), 7.33 (m, 2H), 7.02 (m, 1H), 2.06 (s, 3H); MS(ESI+): m/z 281.16 (M+H)+.

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was partitioned between EtOAc and saturated aq. NaHCO3 solution
washThe EtOAc phase was washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on SiO2 eluting with 30-80% EtOAc in hexanes

Sources & evidence

ORD record: ord-ad378f2c5b3f4233a2f7f2eeba2f711c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714138B2

Reaction notes

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