Tert-Butylamine → 2-[4-(3-Acetoxy-1-butenyl)phenyl]-5-trimethylsilyloxy-pyridine

HRID 1728276Notes

Reaction equation

HRID 1728276 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)=[N:8][CH:9]=1.[C:19]([O:22][CH:23]([CH:25]=[CH2:26])[CH3:24])(=[O:21])[CH3:20].C(N)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>[C:19]([O:22][CH:23]([CH3:24])[CH:25]=[CH:26][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][Si:2]([CH3:18])([CH3:17])[CH3:1])=[CH:9][N:8]=2)=[CH:11][CH:12]=1)(=[O:21])[CH3:20]

Participants

7

Reactant 3

HCID 6385Tert-ButylamineHCID 1388211-Methylallyl acetateHCID 190171025-Trimethylsilyloxy-2-(4-bromophenyl)pyridine

Product 1

HCID 541983492-[4-(3-Acetoxy-1-butenyl)phenyl]-5-trimethylsilyloxy-pyridineYield 74.7%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

17 g of 5-trimethylsilyloxy-2-(4-bromophenyl)pyridine, 12 g of 2-acetoxy-3-butene, 10 g of N-tert.-butylamine, 20 ml of N-methylpyrrolidone, 0.12 g of palladium(II) acetate and 0.3 g of triphenylphosphine are reacted in an analogous manner to Example 1(d) to give 14 g of 2-[4-(3-acetoxy-1-butenyl)-phenyl]-5-trimethylsilyloxy-pyridine.

Sources & evidence

ORD record
ord-50e66bb5ea6c4ff5976320821ca4e934
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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