4-Methoxybenzylamine → HCID 58447313, compound

HRID 1667423Notes

Reaction equation

HRID 1667423 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]=[CH:5]2.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.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+]>C1(C)C=CC=CC=1.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]>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][N:6]=[CH:5]3)=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 754524-MethoxybenzylamineHCID 634876Binap, (A+-)-HCID 115359186-Bromophthalazin-1(2h)-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 58447313HCID 58447313, compoundYield 35.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-2H-phthalazin-1-one (50 mg, 0.22 mmol), 4-methoxybenzylamine (0.030 mL, 0.24 mmol), Pd2(dba)3 (20 mg, 0.022 mmol), rac-BINAP (41 mg, 0.066 mmol) and NaOt-Bu (52 mg, 0.55 mmol) in toluene (10 mL) was heated at reflux for 3 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with NaHCO3 (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound (22 mg, 35%). 1H-NMR (DMSO-d6) δ: 12.1 (s, 1H), 8.05 (s, 1H), 7.88 (d, 1H), 7.30 (m, 3H), 7.10 (dd, 1H), 6.90 (d, 2H), 6.75 (s, 1H), 4.20 (d, 2H), 3.85 (s, 3H); m/z (M+1)=282.22.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. washwashed with NaHCO3 (25 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8feb20dbef1247a78172db24c93cd76e
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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