2-Methoxypropene → HCID 59619684, compound

HRID 445712Notes

Reaction equation

HRID 445712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([CH2:8][CH3:9])=[N:6][CH:7]=1.Br[C:12]1[CH:13]=C(N)C(C)=N[CH:17]=1.CC(C(OCC)=O)C(OCC)=O.COC(C)=C.C(N(CC)CC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:10]=[C:12]([CH3:13])[CH3:17])[C:5]([CH2:8][CH3:9])=[N:6][CH:7]=1

Participants

8

Reactant 6

HCID 83002-MethoxypropeneHCID 8471TriethylamineHCID 11857Diethyl methylmalonateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 219640965-Bromo-2-methylpyridin-3-amineHCID 57545913HCID 57545913, compound

Product 1

HCID 59619684HCID 59619684, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-2-ethyl-pyridin-3-ylamine (1.492 mmol), synthesized in a similar manner as described for 5-bromo-2-methyl-pyridin-3-ylamine (Stage 75.1.4) using diethyl methylmalonate (HPLC: tR 1.71min (Method A); M+H=201, 203 MS-ES), in chloroform (0.75 ml) and 2-methoxypropene (Aldrich, Buchs, Switzerland, 7.46 mmol) were added triethylamine (1.492 mmol) and pyridinium para-toluensulfonate (0.149 mmol). The RM was stirred for 17 h at 100° C., then was quenched with aqueous Na2CO3 and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a brown oil (M+H=241, 243 MS-ES).

Workup

  1. customwas quenched with aqueous Na2CO3
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7b297214a94648588fafd24d8cc9bdc7
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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