6-Bromo-5-fluoropicolinic Acid → HCID 86639737, compound

HRID 2192666Notes

Reaction equation

HRID 2192666 reaction equation
[Si:1]([O:8][C@H:9]1[C@@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@H:13]([CH3:23])[CH2:12][C@@H:11]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[NH2:30])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:31][C:32]1[N:37]=[C:36]([C:38](O)=[O:39])[CH:35]=[CH:34][C:33]=1[F:41]>CCOC(C)=O>[Si:1]([O:8][C@H:9]1[C@@H:14]([O:15][Si:16]([C:19]([CH3:21])([CH3:22])[CH3:20])([CH3:18])[CH3:17])[C@H:13]([CH3:23])[CH2:12][C@@H:11]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[NH:30][C:38](=[O:39])[C:36]2[CH:35]=[CH:34][C:33]([F:41])=[C:32]([Br:31])[N:37]=2)[CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 534011946-Bromo-5-fluoropicolinic AcidHCID 68548666HCID 68548666, compound

Product 1

HCID 86639737HCID 86639737, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following Method 9, 4-((1R,3R,4S,5R)-3,4-bis(tert-butyldimethylsilyloxy)-5-methylcyclohexyl)pyridin-3-amine and 6-bromo-5-fluoropicolinic acid were coupled and following addition of EtOAc and washing with H2O, NaCl(sat.) and drying over MgSO4, N-(4-((1R,3R,4S,5R)-3,4-bis(tert-butyldimethylsilyloxy)-5-methylcyclohexyl)pyridin-3-yl)-6-bromo-5-fluoropicolinamide was obtained. LCMS (m/z): 652.5, 652.4 (MH+); LC Rt=5.82 min.

Workup

  1. washwashing with H2O, NaCl(sat.)
  2. dry with materialdrying over MgSO4

Sources & evidence

ORD record
ord-29b25c13558f40b58c6de87536c41e01
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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