Triethylamine → HCID 178480127, compound

HRID 1480834Notes

Reaction equation

HRID 1480834 reaction equation
CCN(CC)CC.C([SiH](CC)CC)C.C([O:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][N:29]=[C:30]2[C:33]2[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=2)=[CH:25][N:24]=1)C1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:38][N:36]1[CH:37]=[C:33]([C:30]2[N:29]=[CH:28][CH:27]=[C:26]3[C:31]=2[CH:32]=[C:23]([OH:22])[N:24]=[CH:25]3)[CH:34]=[N:35]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 89996289HCID 89996289, compound

Product 1

HCID 178480127HCID 178480127, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of Pd(OAc)2 (4 mg, 0.019 mmol), Et3N (7.5 uL, 0.053 mmol), triethylsilane (0.085 mL, 0.531 mmol) in DCM (8 mL) was stirred at room temperature for 10 minutes. A solution of 7-(benzyloxy)-1-(1-methyl-1H-pyrazol-4-yl)-2,6-naphthyridine (Preparation 88, 120 mg, 0.379 mmol) in DCM (1 mL) was added. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with aqueous saturated ammonium chloride (20 mL) and extracted with ether (2×30 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-10% MeOH in DCM to give the title compound (13 mg, 15%).

Workup

  1. customThe reaction mixture was quenched with aqueous saturated ammonium chloride (20 mL)
  2. extractionextracted with ether (2×30 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-06d6112a0278425d8e55e79f9be1c8b8
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…