Potassium Phosphate, Tribasic → HCID 68328525, compound

HRID 634229Notes

Reaction equation

HRID 634229 reaction equation
[C:1]([NH:5][C:6]1[O:7][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:15]=[C:14]3B2OC(C)(C)C(C)(C)O2)=[N:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:40]1[N:45]=[C:44]([CH:46]2[CH2:48][CH2:47]2)[CH:43]=[CH:42][N:41]=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]([NH:5][C:6]1[O:7][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:15]=[C:14]3[C:40]2[N:45]=[C:44]([CH:46]3[CH2:48][CH2:47]3)[CH:43]=[CH:42][N:41]=2)=[N:9][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 49758247HCID 49758247, compoundHCID 68328226HCID 68328226, compound

Product 1

HCID 68328525HCID 68328525, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

To a 5 mL glass microwave tube containing N-tert-butyl-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 (357.8 mg, 0.667 mmol) was added 2-bromo-4-cyclopropylpyrimidine (153 mg, 0.767 mmol) (CombiPhos Catalysts Inc.), potassium phosphate (425 mg, 2.001 mmol) (Sigma-Aldrich), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (19.08 mg, 0.040 mmol) (Strem), and Pd2(dba)3 (18.32 mg, 0.020 mmol) (Strem). The tube was purged with argon, the solids were treated with Dioxane (3.0 mL) and Water (0.300 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 H2O and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (eluting with 5-60% EtOAc in Hex) affording N-tert-butyl-5-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (86.2 mg, 0.163 mmol, 24.45) as an off-white foam. MS (ESI, pos. ion) m/z: 529.0 (M+1).

Workup

  1. customThe tube was purged with argon
  2. additionthe solids were treated with Dioxane (3.0 mL) and Water (0.300 mL)
  3. customthe tube was sealed
  4. additionThe mixture was treated with H2O
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography (eluting with 5-60% EtOAc in Hex)

Sources & evidence

ORD record
ord-b92f148117d941d69f6cfcc963375e3f
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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