Toluene → HCID 58531469, compound

HRID 1889649Notes

Reaction equation

HRID 1889649 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:30]=[C:31]([O:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[CH:32]=1)[CH2:8][N:9]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[S:10]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=1[OH:21])(=[O:12])=[O:11])=[N+]=[N-].C1(C)C=CC=CC=1>CCOC(C)=O.CO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:30]=[C:31]([O:33][C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[CH:32]=1)[CH2:8][N:9]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)[S:10]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=1[OH:21])(=[O:12])=[O:11]

Participants

6

Reactant 2

HCID 1140TolueneHCID 58531473HCID 58531473, compound

Product 1

HCID 58531469HCID 58531469, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3-(azidomethyl)-5-(4-fluorophenoxy)benzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide (1.0 g, 1.652 mmol) and 100 mg of 20% of Pd(OH)2 on carbon in EtOAc (15 mL) and MeOH (15 mL) was stirred at rt under 1 atm of H2 gas for 3 h. To the mixture was added toluene. The resulting mixture was stirred for a while, and the solid was filtered, washed with methanol. The filtrate was concentrated in vacuo to obtain the desired product (0.88 g, 1.519 mmol, 92% yield) as a white solid. 1H NMR (CD3OD): δ 7.49 (d, J=2.8 Hz, 1H), 7.35 (d, J=2.8 Hz, 1H), 7.21-7.09 (m, 4H), 6.99-6.90 (m, 5H), 6.85 (s, 1H), 6.64 (s, 1H), 4.48 (s, 2H), 4.40 (s, 2H), 3.93 (s, 2H); MS (ESI): (M+H)+=579.0.

Workup

  1. stirringThe resulting mixture was stirred for a while
  2. filtrationthe solid was filtered
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4143406afccd44b79c1eefbb14c86c18
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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