2-Pyridinemethanamine → HCID 24948339, compound

HRID 1803569Notes

Reaction equation

HRID 1803569 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].[NH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=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+]>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:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 195092-PyridinemethanamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948339HCID 24948339, compoundYield 1.8%

Reagents, catalysts & solvents 3

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

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (153 mg, 0.590 mmol), 2-(aminomethyl)pyridine (0.066 mL, 0.646 mmol), Pd2(dba)3 (49 mg, 0.0535 mmol), rac-BINAP (113 mg, 0.181 mmol) and NaOtBu (160 mg, 1.665 mmol) in DMA (5 mL) was heated at 85° C. for 1.5 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 on silica (EtOAc/hexanes) afforded 4-chloro-6-[(pyridin-2-ylmethyl)-amino]-2H-phthalazin-1-one (3 mg) as a yellow brown solid, 1H (400 MHz, d6-DMSO) δ: 4.53 (d, 2H), 6.84 (s, 1H), 7.18 (dd, 1H), 7.28 (m, 1H), 7.38 (d, 1H), 7.75 2H), 7.92 (d, 1H), 8.55 (d, 1H), 12.35 (s, 1H) ppm; m/z (M+1) 286.99.

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-bd1b2bce485841e0a91a5e0c3acfd536
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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