Sodium Carbonate → HCID 59305836, compound

HRID 2241041Notes

Reaction equation

HRID 2241041 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][CH:3]=1.[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.C([O-])([O-])=O.[Na+].[Na+]>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.C1COCC1>[CH3:25][N:26]1[CH:30]=[C:29]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[C:9]3[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:17])([CH3:18])[CH2:10]3)=[CH:6][CH:7]=2)[CH:28]=[N:27]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 68501670HCID 68501670, compound

Product 1

HCID 59305836HCID 59305836, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The procedure described for 22 (Example 11) was employed using 16 (192 mg, 0.5 mmol), Pd(Ph3P)4 (58 mg, 0.05 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (208 mg, 1.0 mmol), 2N aqueous Na2CO3 (0.5 mL, 1.0 mmol), and THF (3 mL). The reaction mixture was refluxed for 12 h. Aqueous work-up followed by flash column chromatography afforded 170 mg (88%) of the title product 23 as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.73 (s, 1H), 7.56 (s, 1H), 7.37 (d, J=8.0 Hz, 2H), 7.26 (d, J=8.8 Hz, 2H), 7.20-7.16 (m, 4H), 3.92 (s, 3H), 2.02 (s, 2H), 1.97 (s, 2H), 1.29 (s, 2H), 0.95 (s, 6H), 0.93 (s, 6H). LCMS (APCI): m/z 385 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h

Sources & evidence

ORD record
ord-13c4f2a1b5e44fa0a42e8d1ef8ad2523
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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