Potassium Carbonate → HCID 89157687, compound

HRID 1468686Notes

Reaction equation

HRID 1468686 reaction equation
Br[C:2]1[C:10]2[S:9][C:8]([NH2:11])=[N:7][C:6]=2[CH:5]=[C:4]([CH3:12])[C:3]=1[O:13][CH3:14].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.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:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:10]3[S:9][C:8]([NH2:11])=[N:7][C:6]=3[CH:5]=[C:4]([CH3:12])[C:3]=2[O:13][CH3:14])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid2×HCID 89158013HCID 89158013, compound

Product 1

HCID 89157687HCID 89157687, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The mixture of 7-bromo-6-methoxy-5-methylbenzo[d]thiazol-2-amine (8A) (1.72 g, 6.32 mmol), 4-chlorophenyl boronic acid (1.2 g, 7.67 mmol), K2CO3 (2.63 g, 18.9 mmol), Pd(PPh3)4 (364 mg, 0.315 mmol) in DME (8 ml) and H2O (4 ml) was reacted in microwave at 110° C. for 1 h. Then 4-chlorophenyl boronic acid (100 mg, 0.64 mmol), Pd(PPh3)4 (100 mg, 0.086 mmol) were added and reacted in microwave at 110° C. for 0.5 h and 120° C. for 20 min. 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 C15H13ClN2OS: 305.0 (M+H+). Found: 305.1 (M+H+).

Workup

  1. customwas reacted in microwave at 110° C. for 1 h
  2. customreacted in microwave at 110° C. for 0.5 h and 120° C. for 20 min
  3. washThe reaction mixture was washed by water
  4. extractionextracted by EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. custompurified by silica gel column
  9. washeluting by 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-6e021cf203d64b3a94ee362e2b89cb93
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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