Sodium sulfate decahydrate → HCID 68532226, compound

HRID 2243388Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[C:18]([NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)=[O:21])=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[C:4]([O:6]C)=O.[CH3:34][Mg]Br.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:4]([C:3]1[C:2]([F:1])=[CH:11][CH:10]=[CH:9][C:8]=1[O:12][C:13]1[C:18]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)=[O:21])=[CH:17][CH:16]=[CH:15][N:14]=1)(=[O:6])[CH3:34]

Participants

Conditions

Temperature: -78 °C

Procedure

Methyl 2-fluoro-6-(3-(3-(4-(trifluoromethoxy)phenyl)ureido)pyridin-2-yloxy)benzoate (250 mg, 0.54 mmol) was diluted in THF (10 mL) and cooled to −78° C. Methylmagnesiumbromide (3.0 M in Et2O, 1.07 mL, 3.22 mmol) was added and mixture was warmed to rt and stirred for 18 h. Sodium sulfate decahydrate was added and stirring was continued for 30 min. The solution was filtered over a pad of Celite® and washed using ethyl acetate. The organic phase was evaporated and crude material was purified using preparative HPLC to yield the desired material (20 mg) (M+H)+=450. 1H NMR (400 MHz, Acetone) δ ppm 2.33-2.40 (m, J=1.77 Hz, 3H), 7.07-7.18 (m, 3H), 7.27 (d, J=8.84 Hz, 2H), 7.56 (td, J=8.34, 6.57 Hz, 1H), 7.63-7.70 (m, 3H), 8.20 (s, 1H), 8.67 (dd, J=7.96, 1.64 Hz, 1H), 8.91 (s, 1H).

Workup

temperaturemixture was warmed to rt
stirringstirring
waitwas continued for 30 min
filtrationThe solution was filtered over a pad of Celite®
washwashed
customThe organic phase was evaporated
customcrude material was purified

Sources & evidence

ORD record: ord-5954856453e94d14b08f9eda28d6deed
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674828B2

Reaction notes

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