Sodium Carbonate → HCID 73291873, compound

HRID 1398044Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[N:8]=1)(=O)=O.CC1(C)COB([C:36]2[C:37]([CH3:44])([CH3:43])[O:38][C:39]([CH3:42])([CH3:41])[CH:40]=2)OC1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH3:26])[N:8]=[C:7]([C:36]3[C:37]([CH3:44])([CH3:43])[O:38][C:39]([CH3:42])([CH3:41])[CH:40]=3)[CH:11]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-(4-Chlorophenyl)-1-(2-methoxyphenyl)-1H-pyrazol-3-yl trifluoromethanesulfonate (Example 65, (c)) (337 mg, 0.78 mmol, 1 eq) in DMF (5 mL) was added 5,5-dimethyl-2-(2,2,5,5-tetramethyl-2,5-dihydro-furan-3-yl)-[1,3,2]dioxaborinane (223 mg, 0.93 mmol, 1.2 eq), sodium carbonate (198 mg, 1.87 mmol, 2.4 eq), and Pd(Ph3P)4 (90 mg, 0.078 mmol, 0.1 eq). Ar was bubbled through and the solution was heated to 100° C. for 5 hrs. Added water, extracted with EtOAc, dried over MgSO4 and conc. Purification by column chromatography (24 g) eluting with 5 to 10% EA/hexanes gave the title compound (249 mg, 78%).

Workup

customAr was bubbled through and the solution
extractionAdded water, extracted with EtOAc
dry with materialdried over MgSO4 and conc. Purification by column chromatography (24 g)
washeluting with 5 to 10% EA/hexanes

Sources & evidence

ORD record: ord-572b5d05500f4427a5335b9e09333233
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901314B2

Reaction notes

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