Triethylamine → HCID 21103206, compound

HRID 1354805Notes

Reaction equation

HRID 1354805 reaction equation
[C:1]1([C:7]2[C:8]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=3)=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC>CS(C)=O.C([O-])(O)=O.[Na+]>[C:1]1([C:7]2[C:8]([C:17]3[CH:18]=[CH:19][C:20]([CH:23]=[O:24])=[CH:21][CH:22]=3)=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 21103208HCID 21103208, compound

Product 1

HCID 21103206HCID 21103206, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of [4-(3-phenyl-1,8-naphthyridin-2-yl)phenyl]methanol (9-2) (289 mg, 0.925 mmole) in DMSO (2 mL) was added Et3N (1.3 mL, 9.25 mmole) then a solution of pyridine-SO3 (442 mg, 2.78 mmole) in DMSO (2 mL). After 1 hr the mixture was diluted with saturated NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with H2O (2×), brine then dried (MgSO4), filtered, and concentrated to give the title compound as a greenish foam which was sufficiently for use in the next step: 1H-NMR (500 MHz, CDCl3) δ 10.02 (s, 1), 9.19 (dd, J=1.95, 2.20 Hz, 1 H), 8.28 (dd, J=1.95, 6.10 Hz, 1 H), 8.26 (s, 1 H), 7.79 (d, J=8.05 Hz, 2 H), 7.73 (d, J=8.30 Hz, 2 H), 7.56 (m, 1H), 7.35 (m, 3 H), 7.27 (m, 2 H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with H2O (2×), brine
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5fbdd0ac6c97419e8ae2b5f72175ebfb
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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