Dimethylformamide → HCID 58303957, compound

HRID 1404094Notes

Reaction equation

HRID 1404094 reaction equation
[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2C(=[C:9]([F:11])[CH:10]=1)NC=[C:5]2[CH2:12][C:13]([O:15][CH2:16]C)=[O:14].[OH-].[K+].I[CH3:23].[CH3:24][N:25]([CH:27]=O)[CH3:26]>>[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:26](=[C:9]([F:11])[CH:10]=1)[N:25]([CH3:24])[CH:27]=[C:5]2[CH:12]([CH3:23])[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 66927142HCID 66927142, compound

Product 1

HCID 58303957HCID 58303957, compound

Procedure

To the solution of 9-1 (prepared according to the same procedure of ethyl 2-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)acetate) (2.0 g, 6.3 mmol) in anhydrous DMF (15 mL) was added KOH (1.12 g, 20 mmol), and iodomethane (1.8 g, 12.7 mmol). The mixture was stirred for 1 h at room temperature. After quenching with water, the reaction mixture was extracted with ethyl acetate (150 mL×3). The combined organic layers were dried over anhydrous sodium sulfate. After filtration and concentration, a residue 9-2 (3.0 g, crude) was obtained as yellow oil which was used for the next step without further purification.

Workup

  1. customTo the solution of 9-1 (prepared
  2. customAfter quenching with water
  3. extractionthe reaction mixture was extracted with ethyl acetate (150 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-b8122d7359814306bcf66bbbde4f1426
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

Loading…