Triethylamine → 1-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-N-[(3-hydroxyphenyl)methyl]-2,3-dihydro-(2S)-1H-indole-2-carboxamide

HRID 253159Notes

Reaction equation

HRID 253159 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.[CH3:18][C:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][C@H:32]2[C:40](Cl)=[O:41])(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]>ClCCl>[CH3:21][C:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][C@H:32]2[C:40]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)=[O:41])(=[O:30])=[O:29])=[CH:26][CH:27]=1)([CH3:18])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 220584273-(Aminomethyl)phenol hydrochlorideHCID 866123011-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-2,3-dihydro-(2S)-1H-indole-2-carbonyl chloride

Product 1

HCID 668468041-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-N-[(3-hydroxyphenyl)methyl]-2,3-dihydro-(2S)-1H-indole-2-carboxamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

54 mg (0.53 mmol) of triethylamine are added to a suspension of 42.26 mg (0.265 mmol) of 3-(aminomethyl)phenol hydrochloride in 8 ml of dichloromethane at ambient temperature, then a solution of 100 mg (0.265 mmol) of 1-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-2,3-dihydro-(2S)-1H-indole-2-carbonyl chloride in 2 ml of dichloromethane is added over 10 minutes. This is left to agitate at ambient temperature for 1 hour. The reaction medium is washed with water, dried on magnesium sulfate, the solvents are evaporated and the evaporation residue is purified by silica column chromatography eluting with the help of a toluene/ethyl acetate mixture (8/2; v/v). The expected product is obtained in the form of a white solid with a yield of 51%.

Workup

  1. waitThis is left
  2. washThe reaction medium is washed with water
  3. customdried on magnesium sulfate
  4. customthe solvents are evaporated
  5. customthe evaporation residue is purified by silica column chromatography
  6. washeluting with the help of a toluene/ethyl acetate mixture (8/2; v/v)

Sources & evidence

ORD record
ord-3ce820595df44cd1a864c66f3ae51e86
Source dataset
uspto-grants-2011_01
Patent number
US07872021B2

Reaction notes

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