6-Bromo-5-fluoropicolinic Acid → tert-butyl (3S,5R)-1-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate

HRID 69993Notes

Reaction equation

HRID 69993 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][C@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:9]1.[Br:30][C:31]1[N:36]=[C:35]([C:37](O)=[O:38])[CH:34]=[CH:33][C:32]=1[F:40]>>[Br:30][C:31]1[N:36]=[C:35]([C:37]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][C@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:9]2)=[O:38])[CH:34]=[CH:33][C:32]=1[F:40]

Participants

3

Reactant 2

HCID 534011946-Bromo-5-fluoropicolinic AcidHCID 68919475tert-butyl (3S,5R)-1-(3-aminopyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate

Product 1

HCID 86669212tert-butyl (3S,5R)-1-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate

Procedure

Following Method 11 of Example 305, tert-butyl (3S,5R)-1-(3-aminopyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate and 6-bromo-5-fluoropicolinic acid were coupled to yield tert-butyl (3S,5R)-1-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate. LCMS (m/z): 624.1/626.1 (MH+).

Sources & evidence

ORD record
ord-20e80f539c254a5e99ef1dfc03c1644f
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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