HCID 66578659, compound → HCID 52950309, compound

HRID 1521872Notes

Reaction equation

HRID 1521872 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[S:19](=[O:22])(=[O:21])[CH2:20][C:11]=3[C:10]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Br-].[S:32]1[CH:36]=[CH:35][N:34]=[C:33]1[Zn+]>C1COCC1>[N:25]1([C:23]([C:10]2[C:11]3[CH2:20][S:19](=[O:22])(=[O:21])[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[C:12]=3[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:33]4[S:32][CH:36]=[CH:35][N:34]=4)[CH:3]=3)[N:9]=2)=[O:24])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 66578659HCID 66578659, compoundHCID 178419763HCID 178419763, compound

Product 1

HCID 52950309HCID 52950309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-bromophenyl)-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (100 mg, 0.20 mmol, 1 eq.) is taken in THF in and bubbled with nitrogen for 5 minutes. To this are added thiazolyl zinc bromide (2 mL), tetrakis(triphenyl phosphine)palladium(0) (12 mg, 0.010 mmol, 0.05 eq.) and the reaction mixture is heated under sealed condition at 65° C. for 4 h. The reaction mixture is filtered through a celite pad, concentrated under reduced pressure and purified by flash chromatography to afford the title compound as a pink solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.18-8.16 (d, J=7.7 Hz, 1H), 8.07 (s, 1H), 8.04-8.02 (d, J=7.7 Hz, 1H), 7.96-7.95 (d, J=3.2 Hz, 1H), 7.87-7.86 (d, J=3.2 Hz, 1H), 7.76-7.72 (t, J=7.9 Hz, 1H), 7.65-7.56 (m, 3H), 6.98-6.96 (d, J=7.7 Hz, 1H), 4.91 (s, 2H), 3.93 (m, 2H), 3.67 (m, 4H), 3.62-3.61 (m, 2H). MS (ESI+): 493.0. HPLC (max plot) 98.44%; Rt 4.02 min.

Workup

  1. custombubbled with nitrogen for 5 minutes
  2. temperaturethe reaction mixture is heated
  3. customunder sealed condition at 65° C. for 4 h
  4. filtrationThe reaction mixture is filtered through a celite pad
  5. concentrationconcentrated under reduced pressure
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ea7725985f2c414ebd3f893971905e21
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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