2-Bromo-5-ethoxypyridine → (S)-N-{1-[4-(5'-Ethoxy-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-phenyl]-ethyl}-acetamide

HRID 1470747Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>CN(C=O)C.CO>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[N:3][CH:4]=1)[CH3:10]

Participants

Conditions

Temperature: 180 °C

Procedure

250 mg (1.24 mmol) 2-Bromo-5-ethoxy-pyridine are added to 250 mg (1.02 mmol) (S)-N-[1-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1). The mixture is heated at 180° C. for 1 h. Subsequently the residue is taken up in DMF/methanol and the mixture is purified using reversed phase HPLC (column: Waters XBridge 5 μM; eluent A: water+0.3% NH4OH, eluent B: MeOH+0.3% NH4OH) to yield the desired product.

Workup

customthe mixture is purified

Sources & evidence

ORD record: ord-88640a09168c4c14ac623be57925e00d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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