Sodium Carbonate → 7-Cyclobutyl-5-(2-phenyl-quinolin-7-yl)-imidazo[5,1-f][1,2,4]triazin-4-ylamine

HRID 1163151Notes

Reaction equation

HRID 1163151 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.[C:16]1([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][C:26](B4OC(C)(C)C(C)(C)O4)=[CH:27][CH:28]=3)[N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH:1]1([C:5]2[N:13]3[C:8]([C:9]([NH2:14])=[N:10][CH:11]=[N:12]3)=[C:7]([C:26]3[CH:25]=[C:24]4[C:29]([CH:30]=[CH:31][C:22]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)=[N:23]4)=[CH:28][CH:27]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 533286247-Cyclobutyl-5-iodo-imidazo[5,1-f][1,2,4]triazin-4-ylamineHCID 536290112-Phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Product 1

HCID 115020537-Cyclobutyl-5-(2-phenyl-quinolin-7-yl)-imidazo[5,1-f][1,2,4]triazin-4-ylamine

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-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline (38 mg, 0.110 mmol), and sodium carbonate (Na2CO3) (30 mg, 0.286 mmol) was evacuated and charged with nitrogen (N2) (3×). To this mixture was quickly added tetrakis(triphenylphosphine)palladium(0) and evacuated and charged with N2 (2×). This mixture was charged with a previously degassed solvent DME/H2O (5:1) (2 mL) and heated overnight at 75° C. The reaction mixture was filtered through an autovial (0.45 μM frit) and washed with MeOH (3×). The filtrate was concentrated in vacuo and purified by mass directed purification (MDP) resulting in the title compound as a pale yellow solid; 1H NMR (CDCl3, 400 MHz) δ 1.96-2.10 (m, 1H), 2.10-2.25 (m, 1H); 2.40-2.56 (m, 2H); 2.60-2.78 (m, 2H); 4.12-4.29 (m, 1H); 5.99 (brs, 2H); 7.42-7.58 (m, 3H); 7.84-8.05 (m, 4H); 8.18 (d, J=7.2 Hz, 2H); 8.28 (d, J=8.4 Hz, 1H); 8.39 (s, 1H); MS (ES+): m/z 393.14 (100) [MH+], HPLC: tR=3.51 min (MicromassZQ, polar—5 min).

Workup

  1. customwas evacuated
  2. additioncharged with nitrogen (N2) (3×)
  3. customevacuated
  4. additioncharged with N2 (2×)
  5. additionThis mixture was charged with a previously degassed solvent DME/H2O (5:1) (2 mL)
  6. filtrationThe reaction mixture was filtered through an autovial (0.45 μM frit)
  7. washwashed with MeOH (3×)
  8. concentrationThe filtrate was concentrated in vacuo
  9. custompurified by mass
  10. custompurification (MDP)

Sources & evidence

ORD record
ord-c8b168c8458844d1b99bfd1d8a3808e9
Source dataset
uspto-grants-2010_10
Patent number
US07820662B2

Reaction notes

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