Water → HCID 69347467, compound

HRID 855263Notes

Reaction equation

HRID 855263 reaction equation
CC([O-])(C)C.[K+].[CH3:7][O:8][C:9](=[O:21])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([C:17]#[C:18][CH3:19])[C:11]=1[NH2:20].O.CCOC(C)=O>CN1C(=O)CCC1>[CH3:7][O:8][C:9]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]2[C:11]=1[NH:20][C:18]([CH3:19])=[CH:17]2)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 69343046HCID 69343046, compound

Product 1

HCID 69347467HCID 69347467, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a cold (−10° C.) solution of t-BuOK (30 mg, 0.27 mmol) in 4 ml NMP was added a solution of 2-amino-5-chloro-3-prop-1-ynylbenzoic acid methyl ester (46 mg, 0.21 mmol) in NMP (2 ml). The reaction mixture was slowly warmed to rt and stirring was continued for 1 h. Water and EtOAc were added and organic phase was separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (9:1 cyclohexane:EtOAc) to give 5-chloro-2-methyl-1H-indole-7-carboxylic acid methyl ester (25 mg, 54%) as a light yellow solid. MS (ISP) 222.3 (M+H)+.

Workup

  1. customorganic phase was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by flash column chromatography (9:1 cyclohexane:EtOAc)

Sources & evidence

ORD record
ord-393597e8f5b84c189a380a4334673f1c
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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