Lithium Chloride → HCID 24830537, compound

HRID 2092139Notes

Reaction equation

HRID 2092139 reaction equation
[CH3:1][Mg]Br.[Cl-].[Li+].[CH3:6][C:7]1[N:8]([C:13]2[N:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([C:30]4[N:35]=[CH:34][C:33]([C:36]5[N:41]=[N:40][C:39]([C:42](=[O:44])[CH3:43])=[CH:38][CH:37]=5)=[CH:32][CH:31]=4)([CH3:29])[CH:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=3)=[CH:15][N:14]=2)[C:9]([CH3:12])=[CH:10][CH:11]=1>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[CH3:6][C:7]1[N:8]([C:13]2[N:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([C:30]4[N:35]=[CH:34][C:33]([C:36]5[N:41]=[N:40][C:39]([C:42]([OH:44])([CH3:1])[CH3:43])=[CH:38][CH:37]=5)=[CH:32][CH:31]=4)([CH3:29])[CH:26]([CH3:27])[CH3:28])=[CH:23][CH:24]=3)=[CH:15][N:14]=2)[C:9]([CH3:12])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 59393652HCID 59393652, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 24830537HCID 24830537, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Methyl magnesium bromide (32.4 mL of a 1.4 M solution in THF:toluene (25:75)) was added to a stirred solution of lithium chloride (1.93 g, 45.4 mmol) and 4z (11.7 g, 22.7 mmol) in THF (70 mL) at 0° C. After approximately 1 h at 0° C., the reaction was quenched by the dropwise addition of 1.0 M hydrochloric acid, and the resulting mixture stirred for 15 min. The resulting mixture was poured slowly into saturated aqueous sodium bicarbonate and extracted with EtOAc. The combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 35%-75% EtOAc/hexanes as eluent) to furnish the title compound 4e. m/z (ES) 533 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.23 (d, 1H, J=2.1 Hz), 8.95 (s, 2H), 8.39 (dd, 1H, J=2.3, 8.5 Hz), 7.89 (d, 1H, J=9.0 Hz), 7.79 (d, 1H, J=8.9 Hz), 7.57 (m, 4H), 7.46 (d, 1H, J=8.5 Hz), 5.92 (s, 2H), 4.20 (s, 1H), 3.22 (m, 1H), 2.38 (s, 6H), 1.81 (s, 3H), 1.70 (s, 6H), 0.93 (d, 3H, J=6.4 Hz), 0.88 (d, 3H, J=6.6 Hz).

Workup

  1. customthe reaction was quenched by the dropwise addition of 1.0 M hydrochloric acid
  2. additionThe resulting mixture was poured slowly into saturated aqueous sodium bicarbonate
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 35%-75% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-2c4ec74d715b4a80b176de175981b418
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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