Sodium Carbonate → 5-(3-Benzyloxy-2-fluoro-phenyl)-7-cyclobutyl-imidazo[5,1-f][1,2,4]triazin-4-ylamine

HRID 17976Notes

Reaction equation

HRID 17976 reaction equation
[CH:1]1([C:5]2[N:13]3[C:8]([C:9]([NH2:14])=[N:10][CH:11]=[N:12]3)=[C:7](I)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:16]([O:23][C:24]1[C:25]([F:39])=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:16]([O:23][C:24]1[C:25]([F:39])=[C:26]([C:7]2[N:6]=[C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[N:13]3[C:8]=2[C:9]([NH2:14])=[N:10][CH:11]=[N:12]3)[CH:27]=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 533286247-Cyclobutyl-5-iodo-imidazo[5,1-f][1,2,4]triazin-4-ylamineHCID 593448771,3,2-Dioxaborolane,2-[2-fluoro-3-(phenylmethoxy)phenyl]-4,4,5,5-tetramethyl-

Product 1

HCID 115528405-(3-Benzyloxy-2-fluoro-phenyl)-7-cyclobutyl-imidazo[5,1-f][1,2,4]triazin-4-ylamine

Reagents, catalysts & solvents 2

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
75 °C

Procedure

A flask was charged with 7-cyclobutyl-5-iodo-imidazo[5,1-f][1,2,4]triazin-4-ylamine (30 mg, 0.095 mmol), 2-(3-benzyloxy-2-fluoro-phenyl)-4,4,5,5- tetramethyl [1,3,2]dioxaborolane (62.5 mg, 0.158 mmol), and sodium carbonate (30 mg, 0.286 mmol) and was evacuated and charged with N2 (3×). This mixture was charged with tetrakis(triphenylphosphine palladium (0) (Pd(PPh3)4 (0)) (36 mg, 0.0318 mmol) and the tube was re-evacuated and charged with N2 (2×). This mixture was then charged with a previously degassed solvent DME/H2O (5:1)(3 mL) and heated to 75° C. for 16 h. The reaction mixture was concentrated in vacuo and dissolved in MeOH/CH3CN (1:1) (5 mL), filtered though a 0.45 μM fritted autovial and submitted for mass directed purification (MDP) resulting in the title compound as a white solid.

Workup

  1. customwas evacuated
  2. additioncharged with N2 (3×)
  3. customthe tube was re-evacuated
  4. additioncharged with N2 (2×)
  5. additionThis mixture was then charged with a previously degassed solvent DME/H2O (5:1)(3 mL)
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. dissolutiondissolved in MeOH/CH3CN (1:1) (5 mL)
  8. filtrationfiltered though a 0.45 μM fritted autovial
  9. custompurification (MDP)

Sources & evidence

ORD record
ord-b6ef54b351c34423871cddc28de58fba
Source dataset
uspto-grants-2010_06
Patent number
US07741324B2

Reaction notes

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