Picolinic acid → HCID 70974722, compound

HRID 517095Notes

Reaction equation

HRID 517095 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](O)=[O:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C.O.C(#N)C.CCOC(C)=O>[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)=[O:20])[CH2:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 1018Picolinic acidHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 450739697-Bromo-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 70974722HCID 70974722, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
23 °C

Procedure

To a suspension of 7-bromo-1,2,3,4-tetrahydro-isoquinoline hydrochloride (500 mgs, 2.0 mmol), pyridine-2-carboxylic acid (322 mgs, 2.61 mmol), HATU (992 mgs, 2.61 mmol), in DMF (2.5 mL) was added NMM (0.7 mL, 6.0 mmol) and the resulting solution was stirred at 23° C. for 3 h. The reaction mixture was then diluted with water/acetonitrile (15:1) and the resulting oil was then taken into EtOAc and washed with 1N HCl, NaHCO3, brine and dried (MgSO4). The mixture was the filtered and concentrated) to provide (7-bromo-3,4-dihydroisoquinolin-2(1H)-yl)(pyridin-2-yl)methanone.

Workup

  1. washwashed with 1N HCl, NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated)

Sources & evidence

ORD record
ord-3ea604f3237f44a58e7d8d875b67f2a7
Source dataset
uspto-grants-2015_08
Patent number
US09115096B2

Reaction notes

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