Tri(butyl)vinylstannane → 6-Methyl-5-vinyl-3-(1-t-butyloxycarbonyl-(2S)-azetidinylmethoxy)pyridine

HRID 365919Notes

Reaction equation

HRID 365919 reaction equation
[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([CH3:21])=[C:18](Br)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:22](C([SnH3])=C(CCCC)CCCC)[CH2:23]CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([CH3:21])=[C:18]([CH:22]=[CH2:23])[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 21115800Tri(butyl)vinylstannaneHCID 229618173-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-methyl-pyridine

Product 1

HCID 229618196-Methyl-5-vinyl-3-(1-t-butyloxycarbonyl-(2S)-azetidinylmethoxy)pyridineYield 56.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The product of 196e (1.0 g, 2.8 mmol) and tributylvinyl tin hydride (0.98 mL, 3.4 mmol) and tetrakis(triphenylphosphine)palladium (161 mg, 0.14 mmol) were as in Example 191a to provide the title compound (0.48 g, 1.58 mmol, 56%) after chromatography (silica gel; hexanes/EtOAc, 4:1): MS (CI/NH3) 305 (M+H)+.

Sources & evidence

ORD record
ord-ef41156a15c44f7f9cab134ec80d8311
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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