5-chloro-N-methoxy-N-methyl-1H-indole-2-carboxamide → HCID 66777278, compound

HRID 1818616Notes

Reaction equation

HRID 1818616 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](N(OC)C)=[O:12])=[CH:5]2.[CH2:17]([Li])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:12])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:5]2

Participants

4

Reactant 2

HCID 230033115-chloro-N-methoxy-N-methyl-1H-indole-2-carboxamideHCID 178506865HCID 178506865, compound

Product 1

HCID 66777278HCID 66777278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of the title compound of Example 1 Step A (ca. 42.6 mmol) in THF (100 mL) was added n-hexyllithium (74 mL, 2.3 M in hexanes, 170.4 mmol) dropwise. The mixture was stirred at −78° C. for 2 h, then was quenched by addition of 2 N aqueous hydrochloric acid. The resulting suspension was allowed to warm to room temperature, then was extracted with ethyl acetate. The organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (10% EtOAc in hexanes) provided the title compound: LCMS B, tr=2.70 min, m/z 264.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.37 (br s, 1H), 7.68 (d, J=2.0 Hz, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.29 (dd, J=9.0, 2.0 Hz, 1H), 7.13 (s, 1H), 2.94 (t, J=7.5 Hz, 2H), 1.78 (quint., J=7.5 Hz, 2H), 1.43-1.29 (m, 6H), 0.89 (t, J=7.0 Hz, 3H).

Workup

  1. customwas quenched by addition of 2 N aqueous hydrochloric acid
  2. temperatureto warm to room temperature
  3. extractionwas extracted with ethyl acetate
  4. concentrationThe organic phase was concentrated in vacuo
  5. customPurification by flash chromatography on silica gel (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ca64ec87ac0a487f9bc490daf30a1cbf
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

Loading…