Sodium Carbonate → HCID 59682040, compound

HRID 1394631Notes

Reaction equation

HRID 1394631 reaction equation
[CH:1]([C:4]1[C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6](B(O)O)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[C:20]([C:23]1[CH:39]=[CH:38][C:26]2[S:27][CH:28]=[C:29](OS(C(F)(F)F)(=O)=O)[C:25]=2[CH:24]=1)(=[O:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Cl-].[Na+].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>[CH:1]([C:4]1[C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6]([C:29]2[C:25]3[CH:24]=[C:23]([C:20](=[O:22])[CH3:21])[CH:39]=[CH:38][C:26]=3[S:27][CH:28]=2)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 10999969HCID 10999969, compoundHCID 59682035Trifluoro-methanesulfonic acid 5-acetyl-benzo[b]thiophen-3-yl ester

Product 1

HCID 59682040HCID 59682040, compoundYield 58.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3,5-Diisopropyl-2-methoxymethoxy-phenyl-boronic acid (470 mg, 1.8 mmol) was dissolved in toluene (15 ml) and ethanol (15 ml). Trifluoro-methanesulfonic acid 5-acetyl-benzo[b]thiophen-3-yl ester (320 mg, 0.99 mmol), tetrakis(triphenylphosphine)palladium(0) (114 mg, 0.1 mmol) followed by some 2M sodium carbonate solution (1.98 mmol) was added to this solution. The reaction was then heated overnight, then poured into brine (20 ml) and extracted with ethyl acetate (2×20 ml). The organic layers were then dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (chromatotron, 4μ plate, 0-10% ethyl acetate in hexanes) to give 1-[3-(3,5-diisopropyl-2-methoxymethoxy-phenyl)-benzo[b]thiophen-5-yl]-ethanone as a yellow oil (228 mg, 58%). An analytical sample was obtained by preparatory thin layer chromatography (5% ethyl acetate in hexanes). 1HNMR (250 MHz, CDCl3): δ 8.23 (s, 1H), 7.85-7.97 (m, 2H), 7.48 (s, 1H), 7.14 (d, 1H, J=1.2),7.04 (d, 1H, J=1.2),4.41 (s, 2H), 3.40 (m, 1H), 2.95 (s, 3H), 2.86 (m, 1H), 2.55 (s, 3H), 1.26 (s, 3H), 1.23 (s, 3H), 1.21, (s, 3H), 1.18 (s, 3H).

Workup

  1. additionwas added to this solution
  2. temperatureThe reaction was then heated overnight
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. dry with materialThe organic layers were then dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (chromatotron, 4μ plate, 0-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a0c574dbc65b4572b48ccc6cbcbc502b
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

Loading…