Oxygen → HCID 19101151, compound

HRID 1590852Notes

Reaction equation

HRID 1590852 reaction equation
O=O.[CH2:3]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)=[C:14]([F:25])[CH:13]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[Li+].CC([N-]C(C)C)C>C1COCC1.CN1C(=O)N(C)CCC1>[CH2:3]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][N:19]=2)=[C:14]([F:25])[CH:13]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 977OxygenHCID 81401-BromooctaneHCID 2724682Lithium diisopropylamideHCID 19768408HCID 19768408, compound

Product 1

HCID 19101151HCID 19101151, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

With atmospheric oxygen and moisture being excluded, 7.9 mmol of 2-(4-octyloxy-2-fluorophenyl)-5-methylpyridine dissolved in THF and, about 15 minutes later, 8.7 mmol of 1-bromooctane are added at -70° C. to a solution of 8.7 mmol LDA (prepared from BuLi and diisopropylamine) in THF in the presence of 1.04 ml of DMPU. The reaction mixture is allowed to heat up to room temperature, stirring is continued for a further hour and working up is carried out as usual.

Workup

  1. waitis continued for a further hour

Sources & evidence

ORD record
ord-6e35e151bd1c4e199ae62cc5d7c06589
Source dataset
uspto-grants-1993_04
Patent number
US05204476

Reaction notes

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