5-Iodo-A-85380, 5-trimethylstannyl N-boc derivative → 3-[5-[[1-(tert-Butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]-5-fluorocinnamic Acid Methyl Ester

HRID 2095317Notes

Reaction equation

HRID 2095317 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[C:10](I)[CH:9]=[C:8]([F:13])[CH:7]=1.[C:15]([O:19][C:20]([N:22]1[CH2:25][CH2:24][C@H:23]1[CH2:26][O:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([Sn](C)(C)C)[CH:33]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(OC(N1CC[C@H]1COC1C=C(C2C=C(CCCO)C=CC=2)C=NC=1)=O)(C)(C)C>>[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]([F:13])[CH:9]=[C:10]([C:32]2[CH:31]=[N:30][CH:29]=[C:28]([O:27][CH2:26][C@@H:23]3[CH2:24][CH2:25][N:22]3[C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH:33]=2)[CH:11]=1

Participants

4

Reactant 3

HCID 105744715-Iodo-A-85380, 5-trimethylstannyl N-boc derivativeHCID 593715313-[3-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]-1-propanolHCID 673095463-Fluoro-5-iodocinnamic Acid Methyl Ester

Product 1

HCID 686115413-[5-[[1-(tert-Butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]-5-fluorocinnamic Acid Methyl Ester

Procedure

This compound is prepared by Stille coupling of 3-fluoro-5-iodocinnamic acid methyl ester and 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine, using the same procedure as described above for the preparation of 3-[3-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]-1-propanol.

Sources & evidence

ORD record
ord-c4c7ba6c0dcc4c7a87b7450f05ae8fe8
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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