Triphenylphosphine → HCID 86683130, compound

HRID 920917Notes

Reaction equation

HRID 920917 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.[F:12][C:13]1[CH:18]=[CH:17][N:16]2[CH:19]=[C:20]([CH2:22][CH2:23]O)[N:21]=[C:15]2[CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:23][CH2:22][C:20]3[N:21]=[C:15]4[CH:14]=[C:13]([F:12])[CH:18]=[CH:17][N:16]4[CH:19]=3)[N:7]=[CH:6][C:5]=2[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86683120HCID 86683120, compoundHCID 86683131HCID 86683131, compound

Product 1

HCID 86683130HCID 86683130, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-bromothieno[2,3-d]pyridazin-4(5H)-one from Example 3.4 (231 mg, 1 mmol), 2-(7-fluoroimidazo[1,2-a]pyridin-2-yl)ethanol from Example a5 (180 mg, 1.00 mmol) and Ph3P (525 mg, 2.00 mmol) was dissolved in THF (6 mL). Then DEAD (0.317 mL, 2.00 mmol) in THF (1 mL) was added. The resulting mixture was stirred at room temperature under nitrogen overnight. The mixture was concentrated and purified on the ISCO Combiflash system using a 40 g C-18 column using the following gradient: A: Water (0.1% NH4HCO3); B: Methanol; 30% B to 80% B over 20 min (160 mg, yield: 17.7%).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified on the ISCO Combiflash system
  3. wait30% B to 80% B over 20 min (160 mg, yield: 17.7%)

Sources & evidence

ORD record
ord-2bd66aea996043219ad286c93189c16a
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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