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Potassium Phosphate, Tribasic → N-tert-butyl-5-(3-(4-ethyl-5-fluoropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

HRID 634236
Notes
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Reaction equation

HRID 634236 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].Cl[C:40]1[N:45]=[C:44]([CH2:46][CH3:47])[C:43]([F:48])=[CH:42][N:41]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[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]([CH2:46][CH3:47])[C:43]([F:48])=[CH:42][N:41]=2)=[N:9][N:10]=1)([CH3:3])([CH3:4])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 190749282-Chloro-4-ethyl-5-fluoropyrimidineHCID 68328226HCID 68328226, compound

Product 1

HCID 68328485N-tert-butyl-5-(3-(4-ethyl-5-fluoropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 75.1%

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst

Conditions

Temperature
130 °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 (166 mg, 0.309 mmol) was added 2-chloro-4-ethyl-5-fluoropyrimidine (78 mg, 0.402 mmol), potassium phosphate (197 mg, 0.928 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (8.9 mg, 0.019 mmol), and Pd2(dba)3 (8.5 mg, 9.28 μmol). The tube was purged with argon, the solids were treated with dioxane (2.5 mL) and water (0.25 mL), the tube was sealed, and the contents were heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 130° C. for 30 min. The mixture was treated with H2O and extracted with EtOAc and 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-ethyl-5-fluoropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (124 mg, 75%) as a light yellow foam. MS (ESI, pos. ion) m/z: 535.1 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 9.16 (1H, s), 8.46-8.53 (2H, m), 8.09 (1H, d, J=8.4 Hz), 7.94-8.00 (1H, m), 7.86 (2H, d, J=8.6 Hz), 7.25 (2H, d, J=8.6 Hz), 4.71 (1H, s), 2.89-2.99 (2H, m), 2.35 (3H, s), 1.50 (9H, s), 1.44 (3H, t, J=7.5 Hz).

Workup

  1. customThe tube was purged with argon
  2. additionthe solids were treated with dioxane (2.5 mL) and water (0.25 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-3ee287657ce348d98c5eb7d52b8822bb
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321756B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes