1,4-Benzodioxan-6-ylamine → HCID 58007533, compound

HRID 1094404Notes

Reaction equation

HRID 1094404 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[O:14]1[C:19]2[CH:20]=[CH:21][C:22](N)=[CH:23][C:18]=2[O:17][CH2:16][CH2:15]1.C([O-])=O.[NH4+]>CO.[Pd]>[O:14]1[C:19]2[CH:20]=[CH:21][C:22]([NH:11][CH2:10][CH2:9][C:6]3[CH:7]=[N:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][CH:5]=3)=[CH:23][C:18]=2[O:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 891481,4-Benzodioxan-6-ylamineHCID 2723923Ammonium formateHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-

Product 1

HCID 58007533HCID 58007533, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5 mmol (6-trifluoromethyl-pyridin-3-yl)-acetonitrile (prepared as per example 47, step 1) and 1.1 eq. 2,3-Dihydro-benzo[1,4]dioxin-6-ylamine in MeOH (20 mL) was treated with ammonium formate (5 eq.) and 10% Pd/C (200 mg) and stirred at 80° C. for 2 h. Filtration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (24%) as a light yellow oil. MS m/e: 325.0 [M+H]+.

Workup

  1. filtrationFiltration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Sources & evidence

ORD record
ord-8fc4cc918d9e411f8838038da0b0fe0a
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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