3-Pyridinemethanamine → HCID 24948342, compound

HRID 1803566Notes

Reaction equation

HRID 1803566 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:17]=[N:18][CH:19]=[CH:20][CH:21]=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.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:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

7

Reactant 4

HCID 310183-PyridinemethanamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948342HCID 24948342, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), 3-(aminomethyl)pyridine (0.064 mL, 0.636 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (115 mg, 0.185 mmol) and NaOtBu (169 mg, 1.759 mmol) in DMA (5 mL) was heated at 85° C. for 2 h. The mixture was allowed to cool, then filtered. Preparatory HPLC afforded 4-chloro-6-[(pyridin-3-ylmethyl)-amino]-2H-phthalazin-1-one hydroformate (31 mg) as a yellow solid, 1H (400 MHz, d6-DMSO) δ: 4.41 (d, 2H), 6.78 (d, 1H), 7.12 (dd, 1H), 7.31 (dd, 1H), 7.60 (t, 1H), 7.10 (m, 1H), 7.88 (d, 1H), 8.09 (s, 1H), 8.41 (dd, 1H), 8.56 (d, 1H), 12.31 (s, 1H) ppm; m/z (M+1) 286.99.

Workup

  1. temperatureto cool
  2. filtrationfiltered

Sources & evidence

ORD record
ord-78cfe347ca6e4839962c0152f93c624c
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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