Potassium Fluoride → HCID 70790601, compound

HRID 1971743Notes

Reaction equation

HRID 1971743 reaction equation
[C:1]([N:5]1[CH2:38][CH2:37][CH2:36][CH2:35][C:8]2[C:9](Br)=[C:10]3[C:19]4[CH:18]=[C:17]([C@@H:20]5[O:24][C:23]([CH3:26])([CH3:25])[O:22][C@H:21]5[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:16]([O:32][CH3:33])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:39])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:45]1[S:46][CH:47]=[CH:48][CH:49]=1)CCC.[F-].[K+]>C1(C)C=CC=CC=1.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>[C:1]([N:5]1[CH2:38][CH2:37][CH2:36][CH2:35][C:8]2[C:9]([C:45]3[S:46][CH:47]=[CH:48][CH:49]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C@@H:20]5[O:24][C:23]([CH3:26])([CH3:25])[O:22][C@H:21]5[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:16]([O:32][CH3:33])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:39])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 70790589HCID 70790589, compound

Product 1

HCID 70790601HCID 70790601, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 750 mg of 21e, 550 mg of 2-(tributylstannyl)-thiophene and 28 mg of tetrakis(triphenylphosphine)palladium(0) in 14 ml of degassed toluene was heated under N2 atmosphere for 16 hr at 110° C. The reaction mixture was cooled, 15 ml of sat. aq. KF was added, and stirring prolonged for 2 hr. The reaction was filtered through Celite, and the product was extracted with ethyl acetate. The organic layer was washed, dried and concentrated and the product purified by chromatography over silicagel (using a gradient of heptane-ethylacetate as eluent). This provided 630 mg of 21f; LC-MS-ESI: [M+1] 607.26. NMR (CDCl3) δ 7.35, 7.08, and 6.93 (3×m, 3, thienyl-H), 6.67 and 7.30 (2×s, 2, Ar—H) 5.35 (d 1, CHO), 3.95 (d, 1, CHO), 3.75 (s, 3, OCH3), 0.20 (m, 2, ethyl ester), 1.28 (t, 3, ethyl ester), 4.60, and 3.80 (2×bm, 2, CH2), 3.55 and 4.15 (2×br.m, 2, CH2), 2.92 and 3.13 (2×b.m, 2, CH2) 1.6-2.0 (bm, 4, 2×CH2), 1.32 and 1.50 (2×s, 6, dimethylketal), 1.57 (s, 9, tertC4H9).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe reaction was filtered through Celite
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed
  5. customdried
  6. concentrationconcentrated
  7. customthe product purified by chromatography over silicagel (

Sources & evidence

ORD record
ord-1916163963fa45619116337353330f7f
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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