6-Bromo-5-fluoropicolinic Acid → HCID 59226530, compound

HRID 2192658Notes

Reaction equation

HRID 2192658 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH:13]([CH3:15])[CH2:12][C:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[NH2:22])=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:23][C:24]1[N:29]=[C:28]([C:30](O)=[O:31])[CH:27]=[CH:26][C:25]=1[F:33]>CCOC(C)=O>[Br:23][C:24]1[N:29]=[C:28]([C:30]([NH:22][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:16]=2[C:11]2[CH2:12][CH:13]([CH3:15])[CH2:14][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH:10]=2)=[O:31])[CH:27]=[CH:26][C:25]=1[F:33]

Participants

4

Reactant 2

HCID 534011946-Bromo-5-fluoropicolinic AcidHCID 67130847HCID 67130847, compound

Product 1

HCID 59226530HCID 59226530, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following Method 9, 4-(3-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl)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, 6-bromo-N-(4-(3-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl)pyridin-3-yl)-5-fluoropicolinamide was obtained. LCMS (m/z): 455.3 (MH+); LC Rt=2.09 min.

Workup

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

Sources & evidence

ORD record
ord-699622a569324961a271e14c809f4545
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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