Hydroxyamine hydrochloride → HCID 86609394, compound

HRID 1784808Notes

Reaction equation

HRID 1784808 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:34]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=O)[CH:12]=[C:13]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH:17]=[CH:18][N:19]4[Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH:14]=2)=[CH:5][CH:4]=1.Cl.[OH:45][NH2:46]>C(O)C>[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:34]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[N:46][OH:45])[CH:12]=[C:13]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH:17]=[CH:18][N:19]4[Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:31]([CH3:33])[CH3:32])[CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 68843885HCID 68843885, compound

Product 1

HCID 86609394HCID 86609394, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone (50 mg, 0.085 mmol) and hydroxyamine hydrochloride (29 mg, 0.42 mmol) in 2 mL of ethanol was heated to reflux. After 2 hrs, the reaction was completed. The solvent was removed under reduced pressure. The crude product was redissolved in EtOAc and washed with 5% NaHCO3 (aq) and brine. The organic phase was dried and concentrated to provide [3-(4-Methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)phenyl]-pyridin-3-yl-methanone oxime which was further purified by prep TLC (10:1 EtOAc/MeOH). [3-(4-Methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]pyridin-3-yl-methanone oxime was hydrolyzed as described above to give [3-hydroxy-5-(1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone oxime. NMR for the mixture of isomers: 1H NMR (400 MHz, CD3OD): δ 8.69 (d, J=1.8 Hz, 0.3H), 8.59 (d, J=1.4 Hz, 0.7H), 8.55 (dd, J=5.1, 1.6 Hz, 0.7H), 8.50 (dd, J=4.9, 1.4 Hz, 0.3H), 7.95 (dt, J=5.0, 2.6 Hz, 0.3H), 7.89 (dt, J=4.9, 2.5 Hz, 0.7H), 7.53 (dd, J=7.8, 4.9 Hz, 0.7H), 7.42 (dd, J=8.1, 4.8 Hz, 0.3H), 7.37-7.32 (m, 1H), 7.23 (d, J=3.2 Hz, 0.3H), 7.22 (d, J=3.2 Hz, 0.7H), 7.20-7.00 (m, 5H), 6.91 (dd, J=2.3, 1.6 Hz, 0.7H), 6.79 (dd, J=2.4, 1.4 Hz, 0.3H), 6.59 (d, J=3.1 Hz, 0.3H), 6.49 (d, J=3.2 Hz, 0.7H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe crude product was redissolved in EtOAc
  3. washwashed with 5% NaHCO3 (aq) and brine
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f204a4fc1199400a9a77315d8cc9ea00
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

Loading…