Potassium Carbonate → HCID 22601722, compound

HRID 2308249Notes

Reaction equation

HRID 2308249 reaction equation
Br[C:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[S:4][C:3]=1[CH:16]1[O:20][CH2:19][CH2:18][O:17]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C.CCCCCC>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([C:2]2[C:6]([CH3:7])=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[S:4][C:3]=2[CH:16]2[O:20][CH2:19][CH2:18][O:17]2)[CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 21226206Ethyl acetate hexaneHCID 22601714HCID 22601714, compound

Product 1

HCID 22601722HCID 22601722, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

2-[3-Bromo-5-(4-methoxyphenyl)-4-methylthien-2-yl]-1,3-dioxolane (7.0 g, 20 mmol), 3-methoxyphenylboronic acid (3.3 g, 22 mmol), K2CO3 (9.1 g, 66 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium [II] (0.8 g, 1 mmol) were combined in 20% aqueous dimethoxyethane (80 mL) and heated at 75° C. After 8 h, the cooled mixture was filtered through Celite and washed with ethyl acetate (200 mL). The filtrate was washed with 1 N aqueous NaOH and brine (200 mL each), dried (K2CO3) and concentrated in vacuo to give the crude product (8.4 g) as a dark oil which was pre-adsorbed on silica gel (15 g). Flash chromatography (105 g silica, gradient 5%-10%-20% ethyl acetate-hexane) gave the title compound (7.2 g, 95%) as a clear, colorless oil.

Workup

  1. filtrationthe cooled mixture was filtered through Celite
  2. washwashed with ethyl acetate (200 mL)
  3. washThe filtrate was washed with 1 N aqueous NaOH and brine (200 mL each)
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product (8.4 g) as a dark oil which

Sources & evidence

ORD record
ord-9d2cb782745c4402991b9acf753e45da
Source dataset
uspto-grants-2004_12
Patent number
US06835745B2

Reaction notes

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