6-Bromo-5-fluoropicolinic Acid → 6-bromo-N-(4-((1R,3S)-3-(1,3-dioxoisoindolin-2-yl)-cyclohexyl)pyridin-3-yl)-5-fluoropicolinamide

HRID 2192659Notes

Reaction equation

HRID 2192659 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH2:9]1.[Br:25][C:26]1[N:31]=[C:30]([C:32](O)=[O:33])[CH:29]=[CH:28][C:27]=1[F:35]>CCOC(C)=O>[Br:25][C:26]1[N:31]=[C:30]([C:32]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C@@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([N:14]3[C:15](=[O:24])[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:22]3=[O:23])[CH2:9]2)=[O:33])[CH:29]=[CH:28][C:27]=1[F:35]

Participants

4

Reactant 2

HCID 534011946-Bromo-5-fluoropicolinic AcidHCID 59226443HCID 59226443, compound

Product 1

HCID 866397336-bromo-N-(4-((1R,3S)-3-(1,3-dioxoisoindolin-2-yl)-cyclohexyl)pyridin-3-yl)-5-fluoropicolinamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following Method 9, 2-(3-(3-aminopyridin-4-yl)cyclohexyl)isoindoline-1,3-dione 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-((1R,3S)-3-(1,3-dioxoisoindolin-2-yl)cyclohexyl)pyridin-3-yl)-5-fluoropicolinamide was obtained. LCMS (m/z): 523.2/525.2 (MH+); LC Rt=3.31 min.

Workup

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

Sources & evidence

ORD record
ord-3ce1082f644145149bd0d4161f523635
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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