Triphenylphosphine → HCID 86683128, compound

HRID 920915Notes

Reaction equation

HRID 920915 reaction equation
[Br:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][N:7]=[CH:6][C:5]=2[S:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OCC)=O)=N\C(OCC)=O.[S:43]1[C:51]2[C:46](=[N:47][C:48]([CH2:52][CH2:53]O)=[CH:49][CH:50]=2)[CH:45]=[CH:44]1>C1COCC1>[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:53][CH2:52][C:48]3[N:47]=[C:46]4[CH:45]=[CH:44][S:43][C:51]4=[CH:50][CH:49]=3)[N:7]=[CH:6][C:5]=2[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86683120HCID 86683120, compoundHCID 86683129HCID 86683129, compound

Product 1

HCID 86683128HCID 86683128, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 3-bromothieno[2,3-d]pyridazin-4(5H)-one (100 mg, 0.433 mmol) from Example 3.3 and triphenylphosphine (227 mg, 0.866 mmol) in THF (2 mL) was added (E)-diethyl diazene-1,2-dicarboxylate (151 mg, 0.866 mmol) dropwise at 0° C. After the addition, the mixture was stirred for 1 h at 0° C. Then 2-(thieno[3,2-b]pyridin-5-yl)ethanol from Example a3 (78 mg, 0.433 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at room temperature overnight. The solution was filtered to obtain the title compound (80 mg, yield 47.1%).

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-8f138477572a4db1ab0c54fdfca11d57
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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