Diethyl Ether → HCID 59277534, compound

HRID 2097200Notes

Reaction equation

HRID 2097200 reaction equation
C([Li])(C)(C)C.CC[O:8][CH2:9][CH3:10].Br[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1C)[NH:17][CH:16]=[C:15]2[CH3:22]>CN(C=O)C>[CH3:22][C:15]1[C:14]2[C:18](=[CH:19][C:20]([CH3:12])=[C:10]([CH:9]=[O:8])[CH:13]=2)[NH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 59277605HCID 59277605, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59277534HCID 59277534, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl lithium (16.7 mL, 28.3 mmol, 1.7 M in pentanes) was added to a dry ether (20 mL) solution of 5-bromo-3,6-dimethyl-1H-indole (1.27 g, 5.67 mmol) at −78° C. under Argon. The mixture was stirred at 0° C. for 30 min then cooled to −78° C. DMF (18 mL) was added and the mixture was stirred at 0° C. for 1 h. The reaction was quenched with cold, saturated NH4Cl solution at −78° C. The mixture was diluted with ether and hexane, washed with brine, dried and evaporated. Crystallization from a CH2Cl2/hexane mixture afforded the title compound (810 mg 82%). 1H NMR (300 MHz, CDCl3) 10.29 (s, 1H), 8.06 (s, 1H), 8.00 (s, br, 1H), 7.15 (1s, 1H), 6.97 (s, 1H), 2.76 (s, 3H), 2.36 (s, 3H).

Workup

  1. temperaturethen cooled to −78° C
  2. stirringthe mixture was stirred at 0° C. for 1 h
  3. customThe reaction was quenched with cold, saturated NH4Cl solution at −78° C
  4. additionThe mixture was diluted with ether and hexane
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customCrystallization from a CH2Cl2/hexane mixture

Sources & evidence

ORD record
ord-1eda22c8b9d4491fb2ae198b6770d1e8
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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