Iodoethane → HCID 59267483, compound

HRID 1945283Notes

Reaction equation

HRID 1945283 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:20])[C:8]([CH3:10])([CH3:9])[O:7][B:6]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[O:5]1.I[CH2:22][CH3:23]>C1COCC1>[CH2:22]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([B:6]3[O:5][C:4]([CH3:20])([CH3:3])[C:8]([CH3:9])([CH3:10])[O:7]3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 59267483HCID 59267483, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension of NaH (43 mg, 1.81 mmol) in THF (4 mL) was added a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (400 mg, 1.65 mmol, Aldrich) in THF (4 mL). The reaction mixture was maintained at 0° C. for 15 min, iodoethane (0.200 mL, 2.47 mmol) was added and the reaction was heated at 50° C. for 30 min. The mixture was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organics were washed with brine, dried (Na2SO4), filtered, and concentrated. Chromatography over silica eluting with 1-8% EtOAc/hexanes afforded the title compound as a white solid. LC-MS: calculated for C16H22BNO2 271.16, observed m/e 273.2 (M+H)+ (Rt 2.09 min).

Workup

  1. temperaturethe reaction was heated at 50° C. for 30 min
  2. customThe mixture was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-589a19a016d34046955a9cedeb636b6c
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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