Diisopropylethylamine → 5-Chloro-2-[N-(1-hydroxyindan-2-yl)carbamoyl]indole

HRID 722257Notes

Reaction equation

HRID 722257 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.CCN(C(C)C)C(C)C.[NH2:23][CH:24]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]1[OH:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:13])[NH:23][CH:24]1[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]1[OH:33])=[CH:5]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 857942-Aminoindan-1-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 218839655-Chloro-2-[N-(1-hydroxyindan-2-yl)carbamoyl]indoleYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-1H-indole-2-carboxylic acid (116 mg, 0.67 mmol) was dissolved in DCM (10 ml) containing DIPEA (0.21 ml, 1.19 mmol) and 2-aminoindan-1-ol (Method 1; 101 mg, 0.67mmol) and HATU (247 mg, 0.67 mmol). The reaction mixture was stirred at room temperature for approximately 18 hours. The resulting solution was washed with water (20 ml) and the aqueous layer extracted with DCM (2×20 ml). The organic extracts were combined, dried over magnesium sulphate and concentrated under reduced pressure to give the title compound (195 mg, 100%) as a white solid.

Workup

  1. washThe resulting solution was washed with water (20 ml)
  2. extractionthe aqueous layer extracted with DCM (2×20 ml)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ae31d6c670b47b5a7bac730ffc0ea24
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

Loading…