Potassium Phosphate, Tribasic → HCID 70982447, compound

HRID 1468687Notes

Reaction equation

HRID 1468687 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([O:18][CH3:19])[C:8]([CH3:20])=[CH:7][C:5]=2[N:6]=1.[CH3:21][C:22]1([CH3:33])[C:26](C)(C)OB(C=C(C)C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:4]3[S:3][C:2]([CH:21]=[C:22]([CH3:33])[CH3:26])=[N:6][C:5]=3[CH:7]=[C:8]([CH3:20])[C:9]=2[O:18][CH3:19])=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 151484474,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolaneHCID 70982168HCID 70982168, compound

Product 1

HCID 70982447HCID 70982447, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The mixture of 2-bromo-7-(4-chlorophenyl)-6-methoxy-5-methylbenzo[d]thiazole (8C) (0.153 g, 0.417 mmol), 4,4,5,5-tetramethyl-2-(2-methylprop-1-enyl)-1,3,2-dioxaborolane (0.256 ml, 1.24 mmol), K3PO4 (0.35 g, 1.66 mmol), PdCl2(dppf) (45 mg, 0.062 mmol) in DME (1 ml) and H2O (0.5 ml) was reacted in microwave at 120° C. for 0.5 h. The reaction mixture was washed by water, extracted by EtOAc. The organic phase was combined, dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes. LCMS-ESI+: calc'd for C19H18ClNOS: 344.1 (M+H+). Found: 344.1 (M+H+).

Workup

  1. customwas reacted in microwave at 120° C. for 0.5 h
  2. washThe reaction mixture was washed by water
  3. extractionextracted by EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. custompurified by silica gel column
  8. washeluting by 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-960288e2750b40e3bcf4e5e2e2c479e3
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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