Chloroform → HCID 66759778, compound

HRID 2234150Notes

Reaction equation

HRID 2234150 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4](/[C:7](/I)=[CH:8]/[CH2:9][S:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])=[C:13]([CH3:24])[CH:12]=2)=[CH:3][CH:2]=1.[S:32]1[C:36]([Sn](CCCC)(CCCC)CCCC)=[CH:35][C:34]2[CH:50]=[CH:51][CH:52]=[CH:53][C:33]1=2.C(Cl)(Cl)Cl.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1CCCCC1.[F-].[K+]>CN(C)C=O.C(OCC)(=O)C>[S:32]1[C:36]([C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:6][CH:5]=2)=[CH:8][CH2:9][S:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[C:13]([CH3:24])[CH:12]=2)=[CH:35][C:34]2[CH:50]=[CH:51][CH:52]=[CH:53][C:33]1=2

Participants

9

Reactant 6

HCID 6212ChloroformHCID 8078CyclohexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 2735461(1-Benzothiophen-2-yl)tributylstannaneHCID 86609666HCID 86609666, compound

Product 1

HCID 66759778HCID 66759778, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl (Z)-[4-[3-(biphenyl-4-yl)-3-iodoallylsulfanyl]-2-methylphenoxy]-acetate (419 mg, 0.770 mmol; example 5, step D-E) and (benzo[b]thiophen-2-yl)-tributyltin (335 mg, 0.792 mmol, prepared according to Morimoto et al.: J. Med. Chem. 44, 3355 (2001)) in dry N,N-dimethylformamide (9 mL) Pd2(dba)3.CHCl3 (23.1 mg, 0.023 mmol) was added. Traces of moisture and oxygen were removed and 0.20M solution of tri(tert.butyl)phosphine in cyclohexane (0.39 mL, 0.098 mmol) was added under atmosphere of nitrogen and the whole mixture was stirred at 50° C. for 10 h and then left stand overnight. The dark solution was poured into 10% aqueous solution of potassium fluoride (30 mL) and subsequently ethyl acetate (40 mL) was added. The layers were separated, the aqueous layer was washed with ethyl acetate (2×15 mL) and the collected organic layers were washed with brine (10 mL), 10% solution of potassium fluoride (20 mL), water (20 mL) and brine (20 mL). The organic solution was dried with anhydrous sodium sulfate and its evaporation gave an oil that was purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 93:7).

Workup

  1. customTraces of moisture and oxygen were removed
  2. waitleft
  3. waitstand overnight
  4. additionwas added
  5. customThe layers were separated
  6. washthe aqueous layer was washed with ethyl acetate (2×15 mL)
  7. washthe collected organic layers were washed with brine (10 mL), 10% solution of potassium fluoride (20 mL), water (20 mL) and brine (20 mL)
  8. dry with materialThe organic solution was dried with anhydrous sodium sulfate and its evaporation
  9. customgave an oil that
  10. customwas purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 93:7)

Sources & evidence

ORD record
ord-43aa08e81e56472ea1a5763a941aa0bc
Source dataset
uspto-grants-2010_05
Patent number
US07709528B2

Reaction notes

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