Cesium carbonate → HCID 58447213, compound

HRID 1803600Notes

Reaction equation

HRID 1803600 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-de69e9838be7451186a0a273ad6da8f5
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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