1-(3-Aminophenyl)ethanol → N-(3-(1-hydroxyethyl)phenyl)-3-(indolin-1-ylsulfonyl)benzamide

HRID 1482859Notes

Reaction equation

HRID 1482859 reaction equation
[N:1]1([S:10]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)(=[O:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH2:22][C:23]1[CH:24]=[C:25]([CH:29]([OH:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1>>[OH:31][CH:29]([C:25]1[CH:24]=[C:23]([NH:22][C:16](=[O:18])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([S:10]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)(=[O:12])=[O:11])[CH:14]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:30]

Participants

3

Reactant 2

HCID 2224611-(3-Aminophenyl)ethanolHCID 38075053-(2,3-dihydro-1H-indole-1-sulfonyl)benzoic acid

Product 1

HCID 66763047N-(3-(1-hydroxyethyl)phenyl)-3-(indolin-1-ylsulfonyl)benzamide

Procedure

3-(indolin-1-ylsulfonyl)benzoic acid (3) (200 mg, 0.66 mmol) and 1-(3-aminophenyl)ethanol (75 mg, 0.55 mmol) using method C. The residue was purified using flash chromatography eluting with 0-50% EtOAc in hexanes. The resulting solid was triturated with dichloromethane/hexanes to give N-(3-(1-hydroxyethyl)phenyl)-3-(indolin-1-ylsulfonyl)benzamide as an off-white solid. Yield: 93 mg (40%). 1H-NMR: 10.46 (s, 1H), 8.37 (s, 1H), 8.25 (d, J=8.0 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.74-7.69 (m, 2H), 7.64 (d, J=8.5 Hz, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.29 (t, J=8.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H), 7.16 (d, J=7.5 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 6.99 (dt, J=7.5, 7.5, 1.0 Hz, 1H), 5.19 (d, J=4.0 Hz, 1H), 4.75-4.68 (m, 1H), 3.98 (t, J=8.5 Hz, 2H), 2.93 (t, J=8.5 Hz, 2H), 1.32 (d, J=6.0 Hz, 3H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-50% EtOAc in hexanes
  3. customThe resulting solid was triturated with dichloromethane/hexanes

Sources & evidence

ORD record
ord-db6ea63500734328b955601d013c1e86
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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