Dichloromethane → HCID 86729658, compound

HRID 717559Notes

Reaction equation

HRID 717559 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[C:10]([C:14]2[N:23]=[C:17]3[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][N:16]3[N:15]=2)[CH:11]=[N:12][CH:13]=1.[CH:24]1(B(O)O)[CH2:26][CH2:25]1.C(Cl)Cl>O1CCOCC1.O>[CH:24]1([C:8]2[CH:9]=[C:10]([C:14]3[N:23]=[C:17]4[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][N:16]4[N:15]=3)[CH:11]=[N:12][CH:13]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2760897Cyclopropylboronic acidHCID 82566418HCID 82566418, compound

Product 1

HCID 86729658HCID 86729658, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Cesium carbonate (0.45 g, 0.0013 mol) was added to a stirred solution of 2-(5-bromopyridin-3-yl)-6-methyl-[1,2,4]triazolo[1,5-a]pyridine (44-2; 0.2 g, 0.00069 mol) and cyclopropylboronic acid (0.119 g, 0.00138 mol) in a mixture of 1,4-dioxan (9 mL) and water (3 mL). The reaction mixture was purged with argon for 20 min. Pd(dppf)2Cl2.DCM (0.028 g, 0.000034 mol) was added and the reaction flask was again purged with argon for 10 min. The reaction mixture was then stirred at 100° C. for 18 h. The reaction mixture was filtered through a filter bed of CELITE and the filter bed was thoroughly washed with ethyl acetate (2×50 mL). The collected organic factions were concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford the title compound. 1H NMR (400 MHz, DMSO) δ 9.08-9.07 (d, J=1.2 Hz, 1H), 8.83 (s, 1H), 8.50-8.49 (d, J=2.4 Hz, 1H), 8.04 (s, 1H), 7.78-7.76 (d, J=8.8 Hz, 1H), 7.57-7.55 (d, J=9.2 Hz, 1H), 2.37 (s, 3H), 2.08-2.05 (m, 1H), 1.08-1.03 (m, 2H), 0.84-0.80 (m, 2H), MS (M+1): 251.2.

Workup

  1. customThe reaction mixture was purged with argon for 20 min
  2. customthe reaction flask was again purged with argon for 10 min
  3. filtrationThe reaction mixture was filtered through a filter bed of CELITE
  4. washthe filter bed was thoroughly washed with ethyl acetate (2×50 mL)
  5. concentrationThe collected organic factions were concentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-02dfa447ffdb4fb7b5da615b1a8cad84
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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