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Cesium carbonate → 6-(3-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1-isopropyl-1H-pyrazol-5-yl)bicyclo[3.1.0]hexan-2-ol

HRID 2203672
Notes
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Reaction equation

HRID 2203672 reaction equation
I[C:2]1[CH:6]=[C:5]([CH:7]2[CH:12]3[CH:8]2[CH2:9][CH2:10][CH:11]3[OH:13])[N:4]([CH:14]([CH3:16])[CH3:15])[N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[C:28]([NH2:31])=[N:29][CH:30]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:31][C:28]1[N:29]=[CH:30][C:25]([C:2]2[CH:6]=[C:5]([CH:7]3[CH:12]4[CH:8]3[CH2:9][CH2:10][CH:11]4[OH:13])[N:4]([CH:14]([CH3:16])[CH3:15])[N:3]=2)=[CH:26][C:27]=1[C:32]([F:35])([F:33])[F:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 118161746(+/-)-6-(3-iodo-1-isopropyl-1H-pyrazol-5-yl)bicyclo[3.1.0]hexan-2-ol

Product 1

HCID 1181616836-(3-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1-isopropyl-1H-pyrazol-5-yl)bicyclo[3.1.0]hexan-2-ol

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of (±)-6-(3-iodo-1-isopropyl-1H-pyrazol-5-yl)bicyclo[3.1.0]hexan-2-ol (30 mg, 90.3 μmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amine (39 mg, 0.14 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (6 mg, 0.009 mmol) and cesium carbonate (59 mg, 0.18 mmol) in 1,4-dioxane (0.5 mL) and water (0.1 mL) was purged with nitrogen. The reaction mixture was heated to 110° C. by microwave irradiation for 20 min. The mixture was concentrated, and the resulting residue was diluted with ethyl acetate (2 mL), and the solution was filtered. The filtrate was concentrated. Purification by preparation HPLC followed by chiral SFC separation afforded the title compounds:

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe resulting residue was diluted with ethyl acetate (2 mL)
  3. filtrationthe solution was filtered
  4. concentrationThe filtrate was concentrated
  5. customPurification
  6. customby preparation HPLC
  7. customfollowed by chiral SFC separation

Sources & evidence

ORD record
ord-b1a57cdd1fa34c70ab3e971a8262add2
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365583B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes