Triphenylphosphine → HCID 19700962, compound

HRID 861965Notes

Reaction equation

HRID 861965 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[S:19]1[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[S:19]1[CH:23]=[CH:22][C:21]([CH2:24][N:10]2[C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[N:14][C:13]=3[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:9]2)=[CH:20]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 123570Thiophene-3-methanolHCID 19700680HCID 19700680, compound

Product 1

HCID 19700962HCID 19700962, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 8-(3-chlorophenyl) pyrido[2,3-d]pyridazin-5-one (0.21 g, 0.82 mmoles) in tetrahydrofuran (25 ml) was added 3-thiophenemethanol (0.085 ml, 0.9 moles) and triphenyl phosphine (0.32 g, 1.22 moles). To this mixture was added a solution of diisopropyl azodicarboxylate (0.24 ml, 1.22 moles) in tetrahydrofuran (5 ml) in a dropwise manner. The solution was stirred for 3 hours at room temperature. The solvent was removed and the residue chromatographed from hot methanol, yielding 0.15 g of 6-(3-thienylmethyl)-8-(3-chlorophenyl) pyrido[2,3-d]pyridazin-5-one, mp 165°-166° C.

Workup

  1. customThe solvent was removed
  2. customthe residue chromatographed from hot methanol

Sources & evidence

ORD record
ord-003f8b4404a94844b439e34c1e9c6d8e
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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