Potassium Carbonate → HCID 86700453, compound

HRID 879644Notes

Reaction equation

HRID 879644 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:43]2[CH:44]=[C:45]3[C:50](=[CH:51][CH:52]=2)[N:49]=[C:48]([NH:53][C:54]([CH:56]2[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]2)=[O:55])[CH:47]=[CH:46]3)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([C:43]4[CH:44]=[C:45]5[C:50](=[CH:51][CH:52]=4)[N:49]=[C:48]([NH:53][C:54]([CH:56]4[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61]4)=[O:55])[CH:47]=[CH:46]5)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86700414(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetateHCID 86700454HCID 86700454, compound

Product 1

HCID 86700453HCID 86700453, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (20.0 mg, 0.038 mmol) and N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-yl)cyclohexanecarboxamide (17.2 mg, 0.045 mmol) in dioxane (0.4 mL) was added Pd(PPh3)4 (2.2 mg, 0.002 mmol) and 2N K2CO3 (79 μL, 0.158 mmol). The reaction was degassed for 5 minutes with N2 and then heated at 90° C. for 10 h. After cooling, the reaction mixture was diluted with EtOAc, extracted with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes) to give the product. LCMS-ESI+: calc'd for C41H41ClN5O4S: 734.3 (M+H+); found: 734.3 (M+H+).

Workup

  1. customThe reaction was degassed for 5 minutes with N2
  2. temperatureAfter cooling
  3. additionthe reaction mixture was diluted with EtOAc
  4. extractionextracted with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes)
  9. customto give the product

Sources & evidence

ORD record
ord-37d53c8959ca4db895f81462fce378a0
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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