1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 67443147, compound

HRID 1667526Notes

Reaction equation

HRID 1667526 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:26]=[N:25][C:24]2[N:23]([CH3:27])[CH2:22][CH2:21][O:20][C:19]=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:26]=[N:25][C:24]4[N:23]([CH3:27])[CH2:22][CH2:21][O:20][C:19]=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 24229654N-Methyl-1-(4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)methanamineHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 67443147HCID 67443147, compoundYield 1.3%

Reagents, catalysts & solvents 3

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

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (275 mg, 1.06 mmol), N-methyl-(4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)methylamine (250 mg, 1.29 mmol), Pd2(dba)3 (113 mg, 0.123 mmol), xantphos (214 mg, 0.370 mmol) and NaOtBu (380 g, 3.696 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-(4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-ylmethyl)-amino]-4a,8a-dihydro-2H-phthalazin-1-one (5 mg) as a yellow solid. 1H (400 MHz, d6-DMSO) δ: 2.98 (s, 3H), 3.18 (s, 3H), 3.38 (t, 2H), 4.18 (t, 2H), 4.6 (s, 2H), 6.81 (d, 1H), 6.90 (d, 1H), 7.37 (dd, 1H), 7.61 (d, 1H), 8.00 (d, 1H), 12.40 (s, 1H) ppm; m/z (M+1) 372.21.

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-3e587b166d3845a1bcc2f7110501cf83
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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