Water → 2-biphenyl-4-yl-1H-indole-7-carboxylic acid

HRID 1470641Notes

Reaction equation

HRID 1470641 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[C:5]=1[NH2:24].CC(C)([O-])C.[K+].O>CN1C(=O)CCC1>[C:15]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:17][C:12]([C:11]2[NH:24][C:5]3[C:6]([CH:10]=2)=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:2])=[O:25])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 667063422-Amino-3-biphenyl-4-ylethynyl-benzoic acid methyl ester

Product 1

HCID 469469872-biphenyl-4-yl-1H-indole-7-carboxylic acidYield 50.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a cold solution of 2-amino-3-biphenyl-4-ylethynyl-benzoic acid methyl ester (300 mg, 0.91 mmol) in NMP (5 mL) was added dropwise a solution of potassium t-butoxide (205 mg, 1.83 mmol) in NMP (5 mL). This reaction mixture was allowed to stir at room temperature for 5 h. After the reaction is completed it was poured into water and pH was adjusted to 2. The resulting precipitate was collected by filtration and was washed with water. Finally it was dried in a vacuum oven to get the 145 mg of 2-biphenyl-4-yl-1H-indole-7-carboxylic acid as a pale yellow coloured solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwas washed with water
  3. customFinally it was dried in a vacuum oven

Sources & evidence

ORD record
ord-0044159c5c9c4c7790a13c638054f69b
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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