Cesium carbonate → HCID 71254770, compound

HRID 1508345Notes

Reaction equation

HRID 1508345 reaction equation
[Cl:1][C:2]1[C:3]([C:15]([O:17]C)=[O:16])=[N:4][S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[F:14].C([O-])([O-])=O.[Cs+].[Cs+].ClC1C(C(OC)=O)=NSC=1Cl>COCCOC.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:3]([C:15]([OH:17])=[O:16])=[N:4][S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[F:14]

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 1244566methyl 4,5-dichloroisothiazole-3-carboxylateHCID 71254886HCID 71254886, compound

Product 1

HCID 71254770HCID 71254770, compoundYield 37%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-chloro-5-(3-chloro-2-fluorophenyl)isothiazole-3-carboxylate: To a solution of Intermediate 50A (0.100 g, 0.472 mmol) and Cs2CO3 (0.461 g, 1.415 mmol) in DME (3.02 mL) and water (0.605 mL) was added methyl 4,5-dichloroisothiazole-3-carboxylate (0.100 g, 0.472 mmol). The solution was purged with Ar for 0.5 h. To the solution was added Pd(PPh3)4 (0.054 g, 0.047 mmol). The reaction mixture was then sealed and heated in microwave for 0.5 h at 100° C. The reaction mixture was then diluted with EtOAc and aqueous layer was decanted. The organic layer was concentrated in vacuo, yielding an oily residue which was purified by silica gel column chromatography to provide the desired product (53 mg, 37%) as a white solid. MS(ESI) m/z: 360.0 (M+H)+.

Workup

  1. customThe solution was purged with Ar for 0.5 h
  2. customThe reaction mixture was then sealed
  3. customwas decanted
  4. concentrationThe organic layer was concentrated in vacuo
  5. customyielding an oily residue which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7f84c1b15b88450ba942651cb295e58a
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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