Sodium Carbonate → HCID 59305835, compound

HRID 2241047Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[CH:9][CH:8]=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH3:39][N:40]1[CH:44]=[C:43](B2OC(C)(C)C(C)(C)O2)[CH:42]=[N:41]1>COCCOC>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:13](=[C:14]2[CH2:19][C:18]([CH3:20])([CH3:21])[CH2:17][C:16]([CH3:22])([CH3:23])[CH2:15]2)[C:10]2[CH:11]=[CH:12][C:7]([C:43]3[CH:42]=[N:41][N:40]([CH3:39])[CH:44]=3)=[CH:8][CH:9]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The Suzuki procedure described for 28 was followed using triflate 25 (150 mg, 0.32 mmol), PdCl2(Ph3P)2 (23 mg, 0.032 mmol), 2 N aqueous Na2CO3 (320 uL, 3.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (334 mg, 1.6 mmol), and DME (2 mL). The mixture was heated at 120° C. for 5 min in the microwave. Aqueous work-up followed by purification gave 116 mg (90%) of the title product 31 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.06 (s, 1H), 7.79 (s, 1H), 7.46 (d, J=8.0 Hz, 2H), 7.2-7.16 (m, 2H), 7.11 (d, J=8.0 Hz, 2H), 3.83 (s, 3H), 1.93 (s, 2H), 1.88 (s, 2H), 1.26 (s, 2H), 0.89 (s, 6H), 0.84 (s, 6H). LCMS (APCI): m/z 403 (M+H)+.

Workup

customAqueous work-up followed by purification

Sources & evidence

ORD record: ord-eaecb5524eb045e69e50b2e51f3375db
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723393B2

Reaction notes

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