(3,5-Dimethoxyphenyl)methanamine → HCID 24948720, compound

HRID 1803551Notes

Reaction equation

HRID 1803551 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:21]=[C:22]([O:24][CH3:25])[CH:23]=1)[CH2:19][NH2:20].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC(N(C)C)=O.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[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:20][CH2:19][C:18]3[CH:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:16]([O:15][CH3:14])[CH:17]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948720HCID 24948720, compoundYield 2.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (105 mg, 0.405 mmol), 3,5-dimethoxybenzylamine (0.64 mL, 0.424 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), rac-BINAP (78 mg, 0.125 mmol) and NaOt-Bu (92 mg, 0.963 mmol) in DMA (6 mL) was heated at 80° C. for 45 minutes. 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 on silica (EtOAc/hexanes) afforded 4-chloro-6-(3,5-dimethoxy-benzylamino)-2H-phthalazin-1-one (3 mg) as a brown solid, 1H (400 MHz, CDCl3) δ: 3.65 (d, 6H), 4.28 (s, 2H), 6.25 (m, 1H), 6.42 (m, 2H), 6.81 (m, 1H), 6.95 (m, 2H), 8.00 (m, 1H), ppm. m/z (M+1) 345.92.

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-243fbb483c874771878f6c63a5f97d88
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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