Lithium → HCID 123309962, compound

HRID 706401Notes

Reaction equation

HRID 706401 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:5]([CH2:8]Cl)=[N:6][CH:7]=1.[C:22]([N:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[CH2:28][C:27]1=[O:35])([CH3:25])([CH3:24])[CH3:23].[Li]>C1COCC1>[C:22]([N:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[CH:28]([CH2:8][C:5]2[C:4]([CH2:10][O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)[C:27]1=[O:35])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 3028194LithiumHCID 71738280HCID 71738280, compoundHCID 898160661-(tert-butyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 123309962HCID 123309962, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 65 (23.84 g, 60.7 mmol) and 54 (17.32 g, 91 mmol) in THF (200 ml) was degassed by vacuum/flush N2 below 5° C. To the solution was added lithium amoxide solution in heptanes (27.4 mL, 40%, 85 mmol) maintaining below 7° C. The reaction was aged below 5° C. for 40 min, then quenched with saturated aqueous NH4Cl (10 mL), diluted with hexane (120 mL). The organic layer was separated, washed with saturated aqueous NH4Cl (100 mL) and water (150 mL), concentrated and purified by silica gel column (0 to 5% AcOEt/hexane) to obtain 69, which was used in the next reaction without further purification. HRMS m/z calcd. for C28H41C1N3O2Si 502.2651 (M+H). found 502.2641

Workup

  1. customby vacuum/flush N2 below 5° C
  2. temperaturemaintaining below 7° C
  3. customquenched with saturated aqueous NH4Cl (10 mL)
  4. additiondiluted with hexane (120 mL)
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous NH4Cl (100 mL) and water (150 mL)
  7. concentrationconcentrated
  8. custompurified by silica gel column (0 to 5% AcOEt/hexane)

Sources & evidence

ORD record
ord-4862c1b9dcf84b6abf8d02460a089476
Source dataset
uspto-grants-2015_11
Patent number
US09174989B2

Reaction notes

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