1-(1H-indol-6-yl)methanamine → HCID 23560776, compound

HRID 1058384Notes

Reaction equation

HRID 1058384 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][NH2:11])[CH:8]=2)[CH:3]=[CH:2]1.[CH3:12][O:13][C:14](=[O:32])[C:15]1[CH:20]=[CH:19][C:18]([C:21](ON2C(=O)CCC2=O)=[O:22])=[CH:17][C:16]=1[Cl:31]>CN(C)C=O>[CH3:12][O:13][C:14](=[O:32])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:11][CH2:10][C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[CH:2][NH:1]3)=[CH:5][CH:6]=2)=[O:22])=[CH:17][C:16]=1[Cl:31]

Participants

4

Reactant 2

HCID 172211011-(1H-indol-6-yl)methanamineHCID 235607681-[[3-Chloro-4-(methoxycarbonyl)benzoyl]oxy]-2,5-pyrrolidinedione

Product 1

HCID 23560776HCID 23560776, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-Indole-6-methanamine (Example 71; 0.9 g, 6.2 mmol) was added to a cooled (˜0° C.) solution of 2-chloro-4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]benzoic acid methyl ester (Example 73; 2.20 g, 7.1 mmol) in N,N-dimethylformamide and the solution was allowed to stir at room temperature overnight. The solvent was evaporated under high vacuum and ethyl acetate was added. The solution was washed in turn with 0.5N lo hydrochloric acid solution, saturated sodium bicarbonate solution and brine, then dried (MgSO4), filtered and evaporated in vacuo to afford 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid methyl ester (2.00 g, 94% yield).

Workup

  1. customThe solvent was evaporated under high vacuum and ethyl acetate
  2. additionwas added
  3. washThe solution was washed in turn with 0.5N
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-2a23c14d8ff84845bff1a660a6afd6e5
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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