Sodium Bicarbonate → HCID 69000600, compound

HRID 1909708Notes

Reaction equation

HRID 1909708 reaction equation
I[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1B(O)O>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.C1(C)C=CC=CC=1.CCO>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]2[CH:15]=[CH:16][C:2]([C:24]3[CH:25]=[CH:26][S:22][CH:23]=3)=[CH:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 44819342HCID 44819342, compound

Product 1

HCID 69000600HCID 69000600, compoundYield 794.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a mixture of 1-(4-iodobenzyl)-4-methoxybenzene (0.300 g, 0.925 mmol), 2N aqueous NaHCO3 solution (1.85 mL, 3.7 mmol), and 2-thiopheneboronic acid (0.237 g, 1.85 mmol) in a solution of toluene/EtOH (17.6/0.8 mL) at ambient temperature under an atmosphere of nitrogen was added tetrakis(triphenylphosphine)palladium(0) (0.107 g, 0.093 mmol). The procedure in Example 15, Step 1 was followed to give the title product as a white solid (2.06 g, 79%): 1H NMR (400 MHz, CDCl3): δ 7.52 (d, 2H, J=8.4 Hz), 7.25 (m, 2H), 7.18 (d, 2H, J=8.4 Hz), 7.11 (d, 2H, J=8.8 Hz), 7.05 (m, 1H), 6.84 (d, 2H, J=8.8 Hz), 3.93 (s, 2H), 3.78 (s, 3H).

Sources & evidence

ORD record
ord-f5bc700fa4c246159c12eacd428e0c19
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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