Sodium Carbonate → HCID 11992570, compound

HRID 2241044Notes

Reaction equation

HRID 2241044 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][C:40]1[C:44](B(O)O)=[C:43]([CH3:48])[O:42][N:41]=1>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>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:13](=[C:14]2[CH2:15][C:16]([CH3:23])([CH3:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH2:19]2)[C:10]2[CH:9]=[CH:8][C:7]([C:44]3[C:40]([CH3:39])=[N:41][O:42][C:43]=3[CH3:48])=[CH:12][CH:11]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 86621472HCID 86621472, compound

Product 1

HCID 11992570HCID 11992570, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The Suzuki procedure described for 21 was employed using triflate 25 (200 mg, 0.425 mmol), Pd(Ph3P)4 (49 mg, 0.0425 mmol), 2 N aqueous Na2CO3 (425 uL, 0.85 mmol), (3,5-dimethyl-4-isoxazolyl)boronic acid (150 mg, 1.06 mmol), and THF (25 mL). The reaction mixture was refluxed for 24 h and cooled to RT. Standard work-up followed by column chromatography afforded 132 mg (74%) of the title product 28 as an off-white solid. 1H NMR (400 MHz, CDCl3): δ7.26-7.21 (m, 2H), 7.17-7.14 (m, 4H), 2.41 (s, 3H), 2.28 (s, 3H), 2.0 (s, 2H), 1.95 (s, 2H), 1.31 (s, 2H), 0.96 (s, 6H), 0.93 (s, 6H). LCMS (APCI): m/z 418 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h

Sources & evidence

ORD record
ord-8483f66e00814848baebfe30c71ec35d
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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