Binap, (A+-)- → HCID 44477249, compound

HRID 2361673Notes

Reaction equation

HRID 2361673 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:17][CH:16]([NH2:18])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Br[C:20]1[CH:21]=[CH:22][C:23]([C:26]([NH:28][CH3:29])=[O:27])=[N:24][CH:25]=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.C(O[K])(C)(C)C>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:15][CH:16]([NH:18][C:20]4[CH:21]=[CH:22][C:23]([C:26]([NH:28][CH3:29])=[O:27])=[N:24][CH:25]=4)[CH2:17]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 634876Binap, (A+-)-HCID 228316205-Bromo-N-methylpyridine-2-carboxamideHCID 44477248HCID 44477248, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 44477249HCID 44477249, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-amine (22 mg, 87 μmol) in degassed toluene (2 ml) was added 5-bromo-N-methylpyridine-2-carboxamide (19 mg, 87 μmol), racemic BINAP (8 mg, 13 μmol), tBuOK (12 mg, 0.10 mmol), followed by Pd2(dba)3 (8 mg, 9 μmol). The reaction was heated at 100° C. for 16 hours, concentrated and purified by FCC (DCM/MeOH/NH3 gradient, 98:2:1 to 95:5:1) giving the title compound as colourless oil (26 mg, 78%).

Workup

  1. concentrationconcentrated
  2. custompurified by FCC (DCM/MeOH/NH3 gradient, 98:2:1 to 95:5:1)

Sources & evidence

ORD record
ord-71197f74633f4caba934600c6818279b
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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