Trifluoroacetic acid → HCID 117667370, compound

HRID 712609Notes

Reaction equation

HRID 712609 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([Br:24])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+].CCOC(C)=O>C(Cl)Cl.O>[Br:24][C:22]1[CH:23]=[C:18]([C:14]2[CH:13]=[C:12]3[C:17](=[N:16][CH:15]=2)[NH:8][CH2:9][CH2:10][CH2:11]3)[CH:19]=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 117667781HCID 117667781, compound

Product 1

HCID 117667370HCID 117667370, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

6-(5-Bromo-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (260 mg, 0.67 mmol) is dissolved in 3.0 mL of DCM and trifluoroacetic acid (1.0 mL, 12 mmol) is added. The mixture is stirred for 21 hrs. Then saturated aqueous NaHCO3 is used to adjust the pH to about 8 and EtOAc (25 mL) along with 15 mL of water are added. The mixture is stirred for 10 min and the aqueous layer is separated and extracted with EtOAc (2×15 ml). The organic layers are combined and concentrated to give 6-(5-bromo-pyridin-3-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine which is used in the next step without puification.

Workup

  1. additionare added
  2. stirringThe mixture is stirred for 10 min
  3. customthe aqueous layer is separated
  4. extractionextracted with EtOAc (2×15 ml)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-96c0182a1c544253b35b505179f97a45
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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