Potassium Phosphate, Tribasic → N-(2-phenylpropan-2-yl)-5-(3-(pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

HRID 634223Notes

Reaction equation

HRID 634223 reaction equation
[C:1]1([C:7]([NH:10][C:11]2[O:12][C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:20]=[C:19]4B3OC(C)(C)C(C)(C)O3)=[N:14][N:15]=2)([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:45]1[N:50]=[CH:49][CH:48]=[CH:47][N:46]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([C:7]([NH:10][C:11]2[O:12][C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:26])=[O:27])[CH:20]=[C:19]4[C:45]3[N:50]=[CH:49][CH:48]=[CH:47][N:46]=3)=[N:14][N:15]=2)([CH3:8])[CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 783452-BromopyrimidineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 68328199N-(2-phenylpropan-2-yl)-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 68327964N-(2-phenylpropan-2-yl)-5-(3-(pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 42.7%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

N-(2-Phenylpropan-2-yl)-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (757.3 mg, 1.265 mmol), 2-bromopyrimidine (221 mg, 1.392 mmol) (Aldrich), potassium phosphate (806 mg, 3.80 mmol) (Sigma-Aldrich), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (36.2 mg, 0.076 mmol) (Strem Chemicals), and Pd2(dba)3 (34.8 mg, 0.038 mmol) (Strem Chemicals) were weighed into a 20 mL glass microwave tube, and the tube was purged with argon. The solids were treated with dioxane (8 mL) and water (0.800 mL), the tube was sealed and the contents were heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 20 min. The mixture was treated with water, extracted with EtOAc (3×50 mL), dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (30-100% EtOAc in Hex) to give N-(2-phenylpropan-2-yl)-5-(3-(pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (297.4 mg, 0.540 mmol, 42.7%). MS (ESI, pos. ion) m/z: 551.2 (M+1).

Workup

  1. customthe tube was purged with argon
  2. additionThe solids were treated with dioxane (8 mL) and water (0.800 mL)
  3. customthe tube was sealed
  4. additionThe mixture was treated with water
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by flash chromatography (30-100% EtOAc in Hex)

Sources & evidence

ORD record
ord-ba7a4cf109534f718336a4570b2bc2c3
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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