Cesium carbonate → HCID 58447213, compound

HRID 1667515Notes

Reaction equation

HRID 1667515 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH2:21])=[O:20].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:21][C:19](=[O:20])[C:18]3[CH:22]=[CH:23][CH:24]=[C:16]([O:15][CH3:14])[CH:17]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 984873-MethoxybenzamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 58447213HCID 58447213, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-bromo-4-chloro-2H-phthalazin-1-one (100 mg, 0.39 mmol), 3-methoxy-benzamide (64 mg, 0.42 mmol), Pd2(dba)3 (36 mg, 0.039 mmol), xantphos (68 mg, 0.12 mmol) and Cs2CO3 (607 mg, 0.98 mmol) in dioxane (5 mL) was purged with nitrogen for 10 min. The mixture was place in a microwave reactor for 5 min. After this time the mixture was filtered and purified by preparative HPLC to yield the title compound hydroformate. m/z (M+H)=329.96, 1H-NMR (DMSO-d6) δ: 12.75 (s, 1H), 10.85 (s, 1H), 8.63 (s, 1H), 8.25 (m, 2H), 7.60 (d, 1H), 7.56 (s, 1H), 7.45 (t, 1H), 7.20 (dd, 1H), 3.85 (s, 3H).

Workup

  1. customwas purged with nitrogen for 10 min
  2. customfor 5 min
  3. filtrationAfter this time the mixture was filtered
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-02e2297d983f4f16ae0ab62cf70235c1
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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