Diphenyl carbonate → HCID 118037000, compound

HRID 1777908Notes

Reaction equation

HRID 1777908 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][C:5]=1[I:14].[C:17](=O)([O:25]C1C=CC=CC=1)[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH3:16][O:15][CH:3]([O:2][CH3:1])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:17]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:25])=[CH:6][C:5]=1[I:14]

Participants

5

Reactant 3

HCID 7597Diphenyl carbonateHCID 2733832Lithium HexamethyldisilazideHCID 118036794HCID 118036794, compound2×

Product 1

HCID 118037000HCID 118037000, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(dimethoxymethyl)-6-iodo-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 52, 97 mg, 0.290 mmol) and diphenyl carbonate (74.6 mg, 0.348 mmol) in THF (2.5 ml) at −78° C. was treated with LHMDS (1 M in THF, 0.334 ml, 0.334 mmol) and stirred for 2 h. The reaction was then allowed to warm to room temperature over 20 min, quenched by addition of sat. aq. NH4Cl and extracted with DCM (2×). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a white solid. (UPLC-MS 3) tR 1.19 min; ESI-MS 455.1 [M+H]+.

Workup

  1. customquenched by addition of sat. aq. NH4Cl
  2. extractionextracted with DCM (2×)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

Sources & evidence

ORD record
ord-09aecc7f71b24af183eec252b6a65cdd
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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