Potassium Carbonate → HCID 59852896, compound

HRID 1670288Notes

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-02fa12bb79fe49539153b8955cfd7d39
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989477B2

Reaction notes

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