Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(4-(1,5-dimethyl-1H-pyrazol-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)acetate

HRID 879402Notes

Reaction equation

HRID 879402 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:16]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[C:15]([C@H:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:14]([CH3:35])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH3:36][N:37]1[C:41]([CH3:42])=[C:40](B(O)O)[CH:39]=[N:38]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>[C:31]([O:30][C@@H:24]([C:15]1[C:14]([CH3:35])=[CH:13][C:11]2[N:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:40]4[CH:39]=[N:38][N:37]([CH3:36])[C:41]=4[CH3:42])=[CH:3][CH:4]=3)[S:9][C:10]=2[C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:25]([O:27][CH2:28][CH3:29])=[O:26])([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 532165971,5-Dimethylpyrazole-4-boronic acidHCID 86700207(S)-ethyl 2-(2-(4-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 86700208(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(4-(1,5-dimethyl-1H-pyrazol-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)acetate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

(S)-ethyl 2-(2-(4-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (50.0 mg, 0.087 mmol), 1,5-Dimethyl-1H-pyrazole-4-boronic acid, pinacol ester (24.7 mg, 0.105 mmol), tetrakis(triphenylphosphine)palladium(0) (15.1 mg, 0.013 mmol), and K2CO3 (36.2 mg, 0.262 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 (0.8 mL) and degassed water (0.2 mL). The reaction mixture was stirred at 100° C. for 2.5 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 C33H35ClN3O3S (M+H+): 588.2; Found: 588.3 (M+H+).

Workup

  1. customflushed with argon three times
  2. additionTo this mixture was added
  3. customdegassed 1,4-dioxane (0.8 mL)
  4. customdegassed water (0.2 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-7e6209a05e7d4ddb9b26433a699781be
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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