Sodium Carbonate → HCID 11992663, compound

HRID 2241045Notes

Reaction equation

HRID 2241045 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+].[O:39]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40]1>C1COCC1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:13](=[C:14]2[CH2:15][C:16]([CH3:22])([CH3:23])[CH2:17][C:18]([CH3:20])([CH3:21])[CH2:19]2)[C:10]2[CH:11]=[CH:12][C:7]([C:41]3[CH:42]=[CH:43][O:39][CH:40]=3)=[CH:8][CH:9]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 86621472HCID 86621472, compound

Product 1

HCID 11992663HCID 11992663, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described for 28 was utilized using triflate 25 (150 mg, 0.319 mmol), PdCl2 (Ph3P)2 (23 mg, 0.032 mmol), 2 N aqueous Na2CO3 (320 uL, 0.638 mmol), 3-furanylboronic acid (71 mg, 0.638 mmol), and THF (10 mL). The reaction mixture was refluxed for 15 h. Standard work-up followed by purification gave 50 mg (40%) of the title product 29 (40%) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.71 (s, 1H), 7.45 (s, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.18-7.12 (m, 4H), 6.96 (app. t, J=8.4 Hz, 2H), 6.68 (s, 1H), 2.0 (s, 2H), 1.96 (s, 2H), 1.30 (s, 2H), 0.94 (s, 6H), 0.93 (s, 6H). LCMS (APCI): m/z 389 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-e493a34a75af46e4b82742baeb47eab3
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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