N-Methylisobutylamine → HCID 69047517, compound

HRID 2383499Notes

Reaction equation

Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][CH:3]=1.[CH2:16]([NH:20][CH3:21])[CH:17]([CH3:19])[CH3:18].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:16]([N:20]([CH3:21])[C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][CH:3]=1)[CH:17]([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

5 ml of (4-bromophenoxy)-t-butyldimethylsilane, 2.9 ml of isobutylmethylamine, 458.0 mg of palladium acetate, 1.2 g of 2-(di t-butylphosphino)biphenyl and 2.9 g of sodium t-butoxide were suspended in 40 ml of anhydrous toluene, and the mixture was stirred at 100° C. for 1.5 hours. The catalyst was filtered, followed by addition of water and extraction with ethyl acetate. After the extraction solution was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=1/40→1/20) to give the title compound (3.83 g, 64% yield).

Workup

filtrationThe catalyst was filtered
additionfollowed by addition of water and extraction with ethyl acetate
washAfter the extraction solution was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off
customthe resulting residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=1/40→1/20)

Sources & evidence

ORD record: ord-39bc8afd2efa4836b494bc24a2baa64e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263631B2

Reaction notes

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