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Tris(furan-2-yl)phosphane → Tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate

HRID 624772
Notes
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Reaction equation

HRID 624772 reaction equation
[CH:1]1([N:4]([C:12]2[N:17]3[N:18]=[CH:19][CH:20]=[C:16]3[N:15]=[C:14](SC)[N:13]=2)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>S1C=CC=C1C([O-])=O.[Cu+].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]>[CH:1]1([N:4]([C:12]2[N:17]3[N:18]=[CH:19][CH:20]=[C:16]3[N:15]=[C:14]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([O:25][C:24]([F:23])([F:35])[F:36])[CH:27]=3)[N:13]=2)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 67216767Tert-butyl cyclopropyl(2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate

Product 1

HCID 67216572Tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamateYield 85.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 11194830Cuprous 2-thiophenecarboxylateCatalyst

Conditions

Temperature
50 °C

Procedure

Note: THF was degassed with a stream of N2 for 10 min. in a separate flask. Tert-butyl cyclopropyl(2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate (100 mg, 0.31 mmol), 3-(trifluoromethoxy)phenyl boronic acid (154 mg, 0.74 mmol), tri(2-furyl)phosphine (86 mg, 0.37 mmol), copper(I) thiophene-2-carboxylate (167 mg, 0.88 mmol), Pd2dba3 (24 mg, 0.03 mmol) were combined. The flask was evacuated and backfilled with N2. THF (3.7 mL) was added and the reaction was heated to 50° C. for 5 d. The solution was diluted with Et2O (40 mL) and washed with 10% NH4OH (3×30 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The solid residue was triturated with Et2O and filtered. The filtrate was concentrated in vacuo and purified via flash column chromatography (2.5-5% EtOAc/hexanes) to afford tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate (116 mg, 85%). LCMS (ES): >95% pure, m/z 436 [M+1]+.

Workup

  1. customTHF was degassed with a stream of N2 for 10 min. in a separate flask
  2. customThe flask was evacuated
  3. additionTHF (3.7 mL) was added
  4. additionThe solution was diluted with Et2O (40 mL)
  5. washwashed with 10% NH4OH (3×30 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid residue was triturated with Et2O
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated in vacuo
  12. custompurified via flash column chromatography (2.5-5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9b233a5446a74ce797a1788184137f3e
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09303033B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes