Benzylamine → HCID 90047615, compound

HRID 1507600Notes

Reaction equation

HRID 1507600 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:14])[C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[C:5]2=[CH:4][CH:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+].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>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.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:15]([NH:22][C:2]1[N:7]=[C:6]2[N:8]([CH3:14])[C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[C:5]2=[CH:4][CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 634876Binap, (A+-)-HCID 21931732HCID 21931732, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 90047615HCID 90047615, compound

Reagents, catalysts & solvents 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a mixture of 6-chloro-1,3,3-trimethyl-1H-pyrrolo[2,3-b]pyridin-2-one (500 mg, 2.37 mmol), benzylamine (763 mg, 778 μl, 7.12 mmol) and sodium tert-butoxide (388 mg, 4.03 mmol) in toluene (10 ml) were added tris(dibenzylideneacetone)dipalladium (0) chloroform adduct (49.1 mg, 47.5 μmol) and BINAP (29.6 mg, 47.5 μmol). The reaction mixture was heated to 115° C. and stirred for 48 hours. The reaction mixture was diluted with EtOAc, silica gel was added and the mixture concentrated in vacuo. The obtained material was purified silica gel chromatography using heptane/ethyl acetate as eluent. The title compound was obtained as light yellow solid (616 mg).

Workup

  1. additionwas added
  2. concentrationthe mixture concentrated in vacuo
  3. customThe obtained material was purified silica gel chromatography

Sources & evidence

ORD record
ord-2f395557cb74488dabc52a59b21c2b3f
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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