2-(Tri-n-butylstannyl)thiophene → HCID 66919971, compound

HRID 1971749Notes

Reaction equation

HRID 1971749 reaction equation
[C:1]([N:5]1[CH2:31][CH2:30][CH2:29][CH2:28][C:8]2[C:9](Br)=[C:10]3[C:19]4[CH:18]=[C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[C:16]([O:25][CH3:26])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)CCC>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[CH2:31][CH2:30][CH2:29][CH2:28][C:8]2[C:9]([C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[C:16]([O:25][CH3:26])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 66919892HCID 66919892, compound

Product 1

HCID 66919971HCID 66919971, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 50 mg of 23e, 60 mg of 2-tributylstannylthiophene and 10 mg of tetrakis(triphenylphosphine)palladium(0) in 2 ml of toluene was heated at 125° C. for 16 hr under a nitrogen atmosphere. Reaction was cooled and applied onto silica gel column and eluted with a gradient of toluene/acetone. The fractions containing the product were pooled and concentrated and the remainder crystallized from ethylacetate/ether, providing 34 mg of 23f; Mp: 223-224° C. Rf 0.55 (toluene/acetone 2/1). LC-MS-ESI: [M+1] 527.08. NMR (CDCl3) δ 6.82 and 7.63 (2×s, Ar—H), 6.92, 7.16 and 7.41 (3×m 3, thienyl-H), 1.12 (t, 3, ethyl), 3.22 (m, 3, ethyl), 3.94 (s, 3, OCH3), 4.70 (bm, 1, CH2,) 3.80 (bm, 2, CH2), 3.55 (bm, 1, CH2), 3.02 and 3.20 (2×b.m, 2, CH2), 2.55 (b.m, 2, CH2), 1.60-2.00 (b.m, 4, CH2), 1.56 (s, 9, tertC4H9).

Workup

  1. customReaction
  2. temperaturewas cooled
  3. washeluted with a gradient of toluene/acetone
  4. additionThe fractions containing the product
  5. concentrationconcentrated
  6. customthe remainder crystallized from ethylacetate/ether

Sources & evidence

ORD record
ord-6caec68be0894cde8e7fc3fd2e740ae5
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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