Hexane → HCID 54423542, compound

HRID 1908663Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1.C([Li])CCC.CCCCCC.CON(C)[C:26](=[O:28])[CH3:27].[NH4+].[Cl-]>C1COCC1>[CH:9]([O:8][C:5]1[N:6]=[CH:7][C:2]([C:26](=[O:28])[CH3:27])=[CH:3][CH:4]=1)([CH3:11])[CH3:10]

Participants

Conditions

Temperature: -66 °C

Procedure

A round-bottomed flask was charged with 5-bromo-2-iso-propoxypyridine (IM1) (5.00 g, 23.1 mmol) in THF (100) under N2 and cooled in an acetone/dry-ice bath to −66° C. (internal temperature). A solution of 2.5 M n-butyllithium in hexane (10.1 mL, 25.3 mmol) was added drop wise over 10 minutes at keeping the internal temperature below −55° C. The mixture was stirred at −65° C. for 15 minutes. N-methoxy-N-methylacetamide (3.07 mL, 28.9 mmol) dissolved in THF (10 mL) was then added drop wise over 10 minutes while keeping the internal temperature below −65° C. After stirring for 1 h the mixture was allowed to reach room temperature. The mixture was poured into saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and evaporated to dryness. Flash chromatography (silica, heptanes/EtOAc 4:1) gave the title compound as a colorless oil (3.20 g, 77%) sufficiently pure for the next step.

Workup

customthe internal temperature below −55° C
additionwas then added drop wise over 10 minutes
customthe internal temperature below −65° C
stirringAfter stirring for 1 h the mixture
customto reach room temperature
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
customevaporated to dryness

Sources & evidence

ORD record: ord-995b1124c9e44605a9a82807812717e1
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598213B2

Reaction notes

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