Dimethylamine → (5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine

HRID 1159820Notes

Reaction equation

HRID 1159820 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8](S(C3C=CC=CC=3)(=O)=O)[CH:7]=[CH:6][C:5]=2[C:4]=1[CH:21]=O.[CH3:23][NH:24][CH3:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl.[OH-].[Na+]>[CH3:1][O:2][C:3]1[C:4]([CH2:21][N:24]([CH3:25])[CH3:23])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2

Participants

7

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86618256HCID 86618256, compound2×

Product 1

HCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-Methoxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (366 mg, 1.16 mmol; Intermediate 75) was dissolved in DCE, dimethylamine (3.48 mmol as 2M in MeOH) and sodium triacetoxyborohydride (738 mg, 3.48 mmol) was added in sequence. The reaction mixture was left stirring at r.t. for 23 h, diluted with DCM, NaOH (2M aq) was added until sustained pH at 10. The organic phase was separated, and the water-phase extracted once DCM. The combined organic phases were dried over Na2SO4 and purified by preparative HPLC. Yield: 57 mg residue mauve color

Workup

  1. waitThe reaction mixture was left
  2. additionwas added
  3. customThe organic phase was separated
  4. extractionthe water-phase extracted once DCM
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-85e3296e56784b0c8b77152152698b79
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…