Potassium Carbonate → HCID 22601714, compound

HRID 2308248Notes

Reaction equation

HRID 2308248 reaction equation
[Br:1][C:2]1[C:6]([CH3:7])=[C:5](I)[S:4][C:3]=1[CH:9]1[O:13][CH2:12][CH2:11][O:10]1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=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]>[Br:1][C:2]1[C:6]([CH3:7])=[C:5]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[S:4][C:3]=1[CH:9]1[O:13][CH2:12][CH2:11][O:10]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 21226206Ethyl acetate hexaneHCID 22601716HCID 22601716, compound

Product 1

HCID 22601714HCID 22601714, compoundYield 81%

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-iodo-4-methylthien-2-yl)-1,3-dioxolane (12.4 g, 33.1 mmol), 4-methoxyphenylboronic acid (5.5 g, 36 mmol), K2CO3 (15 g, 110 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium [II] (1.3 g, 1.6 mmol) were combined in 20% aqueous dimethoxyethane (130 mL) and heated at 75° C. After 3 h, the cooled mixture was filtered through Celite and washed with ethyl acetate (350 mL). The filtrate was washed with 1 N aqueous NaOH and brine (350 mL each), dried (K2CO3) and concentrated in vacuo to give the crude product (13.1 g) as a dark solid which was pre-adsorbed on silica gel (40 g). Flash chromatography (600 g silica, gradient 2.5%-5% ethyl acetate-hexane) gave the title compound (9.5 g, 81%, m.p. 103-04° C.) as a white crystalline solid.

Workup

  1. filtrationthe cooled mixture was filtered through Celite
  2. washwashed with ethyl acetate (350 mL)
  3. washThe filtrate was washed with 1 N aqueous NaOH and brine (350 mL each)
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product (13.1 g) as a dark solid which

Sources & evidence

ORD record
ord-a0b6a0373fa04913b405dd05bdaf64b1
Source dataset
uspto-grants-2004_12
Patent number
US06835745B2

Reaction notes

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