Water → HCID 58432990, compound

HRID 388420Notes

Reaction equation

HRID 388420 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:10][S:11][C:12]=1Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:10][S:11][C:12]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 58432991HCID 58432991, compound

Product 1

HCID 58432990HCID 58432990, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Starting material 9 (1.12 g) is dissolved in DME (12 ml) and to this are added 439 mg of 10, water (5 ml) and 954 mg of Na2CO3. The mixture is degassed with argon for 5 min. Pd(dppf)Cl2 (121 mg) is added, the tube is sealed and the reaction mixture is heated at 100° C. in the microwave for 15 min. TLC (Hep/EtOAc, 80/20) shows a good conversion into a slower moving spot. The reaction mixture is diluted with EtOAc and washed with water and brine. The organic layer is dried and concentrated. The residue is purified by flash column chromatography using 5% diisopropyl ether in heptane as eluent. Isothiazole 11 is obtained in good yield as a white crystalline solid.

Workup

  1. customThe mixture is degassed with argon for 5 min
  2. additionPd(dppf)Cl2 (121 mg) is added
  3. customthe tube is sealed
  4. additionThe reaction mixture is diluted with EtOAc
  5. washwashed with water and brine
  6. customThe organic layer is dried
  7. concentrationconcentrated
  8. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-38de0480735640dc9bfc82ce695daaf3
Source dataset
uspto-grants-2013_02
Patent number
US08377953B2

Reaction notes

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