Potassium Carbonate → (S)-ethyl 2-(2-(4-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879401Notes

Reaction equation

HRID 879401 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]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[Br:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>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>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([C:2]2[S:3][C:4]3[C:10]([C:11]4[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=4)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=3[N:6]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 86700207(S)-ethyl 2-(2-(4-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
75 °C

Procedure

(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (200 mg, 0.403 mmol), 4-bromophenylboronic acid (113 mg, 0.564 mmol), tetrakis(triphenylphosphine)palladium(0) (69.8 mg, 0.060 mmol), and K2CO3 (167 mg, 1.208 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed 1,4-dioxane (4 mL) and degassed water (1 mL). The reaction mixture was stirred at 75° C. for 5 h, filtered through Celite (ethyl acetate eluent), and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+ calc'd for C28H28BrClNO3S (M+H+): 572.1 and 573.9; Found: 574.2 (M+H+).

Workup

  1. customflushed with argon three times
  2. additionTo this mixture was added
  3. customdegassed 1,4-dioxane (4 mL)
  4. customdegassed water (1 mL)
  5. filtrationfiltered through Celite (ethyl acetate eluent)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
  8. customprovided the product

Sources & evidence

ORD record
ord-230c8eb8f40946e98b60b7037541dd02
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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