Cesium carbonate → [5-(6-Phenethyloxypyridazin-3-yl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl](2-trifluoromethylphenyl)methanone trifluoroacetate

HRID 1186782Notes

Reaction equation

HRID 1186782 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]1[C:12]2[CH2:13][NH:14][CH2:15][C:11]=2[CH2:10][N:9]1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25])=[O:17].Cl[C:29]1[N:30]=[N:31][C:32]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:33][CH:34]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:36]([O:35][C:32]1[N:31]=[N:30][C:29]([N:14]2[CH2:13][C:12]3[CH2:8][N:9]([C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:25])[F:26])=[O:17])[CH2:10][C:11]=3[CH2:15]2)=[CH:34][CH:33]=1)[CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 431280563-Chloro-6-phenethyloxypyridazineHCID 86661599(3,4,5,6-Tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)(2-trifluoromethylphenyl)methanone trifluoroacetate

Product 1

HCID 86661600[5-(6-Phenethyloxypyridazin-3-yl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl](2-trifluoromethylphenyl)methanone trifluoroacetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(3,4,5,6-Tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)(2-trifluoromethylphenyl)methanone trifluoroacetate (example 1b) (500 mg, 1.26 mmol), 3-chloro-6-phenethyloxypyridazine (example 4a) (296 mg, 1.26 mmol), tris(dibenzylideneacetone)dipalladium(0)chloroform adduct (67.9 mg, 65.6 μmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (81.7 mg, 131 μmol) and cesium carbonate (1.645 g, 5.048 mmol) were stirred in 5 ml of dioxane under an argon atmosphere at 80° C. for 4 h. The reaction mixture was concentrated and admixed with ethyl acetate and water, and the organic phase was removed, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 104 mg (14%), M+H+: 481.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe organic phase was removed
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-79ac0ad47daa40c4be5e61ea580f5ddd
Source dataset
uspto-grants-2014_03
Patent number
US08673917B2

Reaction notes

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