1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 67443003, compound

HRID 1667525Notes

Reaction equation

HRID 1667525 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][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[N:28][CH:27]=[C:26]([CH3:30])[N:25]=2)[CH:18]=1.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.CC([O-])(C)C.[Na+]>O1CCOCC1.CCOC(C)=O.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[CH:4]2[CH:9]([CH:10]=[CH:11][C:2]([N:15]([CH3:14])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]4[CH:29]=[N:28][CH:27]=[C:26]([CH3:30])[N:25]=4)[CH:18]=3)=[CH:3]2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 24229685N-Methyl-1-{3-[(6-methylpyrazin-2-yl)oxy]phenyl}methanamineHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 67443003HCID 67443003, compoundYield 1.7%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (225 mg, 0.867 mmol), N-methyl-3-[(6-methylpyrazin-2-yl)oxy]benzylamine (250 mg, 1.09 mmol), Pd2(dba)3 (95 mg, 0.104 mmol), xantphos (180 mg, 0.312 mmol) and NaOtBu (300 g, 3.12 mmol) in dioxane (6 mL) was heated at 80° C. for 3.5 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography (Hexanes/EtOAc) afforded 4-chloro-6-{methyl-[3-(6-methyl-pyrazin-2-yloxy)-benzyl]-amino}-4a,8a-dihydro-2H-phthalazin-1-one (6 mg) as a yellow solid. 1H (400 MHz, d6-DMSO) δ: 2.27 (s, 3H), 3.24 (s, 3H), 4.83 (s, 2H), 6.88 (d, 1H), 7.03 (s, 1H), 7.07 (d, 1H), 7.12 (d, 1H), 7.32 (dd, 1H), 7.40 (t, 1H), 8.00 (d, 1H), 8.24 (d, 2H), 12.41 (s, 1H) ppm; m/z (M+1) 408.27.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

Sources & evidence

ORD record
ord-503ed4a7b25342dfb34ff3d7da2a9d2c
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

Loading…