849630-82-6 → HCID 59639728, compound

HRID 268686Notes

Reaction equation

HRID 268686 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:10]=1)[NH:7][C:6](=O)[C:5]2=O.[Li+].[BH4-].C1COCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 39082924849630-82-6HCID 131718764lithium borohydride THF

Product 1

HCID 59639728HCID 59639728, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 5-bromo-7-isopropylindoline-2,3-dione (45.1 g, 0.17 mol) in THF (275 ml) at room temperature under a nitrogen atmosphere, was added, via syringe, 2.0 M solution of LiBH4/THF (215 ml) over 30 min. The reaction mixture was stirred at 90° C. for 1 hr, cooled, quenched with distilled water and 5% HCl, and extracted with EtOAc. The extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by elution from a silica gel column with hexane/EtOAc (9:1) to give (14.5 g, 36%) of the product. 1H NMR (300 MHz, CDCl3) δ 8.18 (b, NH), 7.62 (d, 1H), 7.21 (t, 1H), 7.16 (d, 1H), 6.51 (dd, 1H), 3.20 (m, 1H), 1.38 (d, 6H); ESI (+) MS m/e=239 (MH+), ESI (−) MS m/e=237 (MH−).

Workup

  1. temperaturecooled
  2. customquenched with distilled water and 5% HCl
  3. extractionextracted with EtOAc
  4. washThe extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by elution from a silica gel column with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-9c9b891b756146a9a64a294eb58338a3
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

Loading…