Potassium Phosphate, Tribasic → 6-chloro-3-methoxy-4-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588148Notes

Reaction equation

HRID 588148 reaction equation
Cl[C:2]1[C:7]2[C:8]([O:30][CH3:31])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:5]=[C:4]([Cl:32])[N:3]=1.[CH3:33][C:34]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[CH:36][N:35]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].C1COCC1.O>[Cl:32][C:4]1[N:3]=[C:2]([C:38]2[CH:37]=[CH:36][N:35]=[C:34]([CH3:33])[CH:39]=2)[C:7]2[C:8]([O:30][CH3:31])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:5]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 1182725104,6-dichloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1182725626-chloro-3-methoxy-4-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 3

HCID 54751079XPhos PalladacycleCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4,6-dichloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (37B, 75 mg, 0.163 mmol), 2-methylpyridine-4-boronic acid pinacol ester (39.3 mg, 0.179 mmol), and Xphos Precatalyst 2nd generation (10.25 mg, 0.013 mmol) were taken up in THF (1.1 ml). The mixture was evacuated and back-filled with N2 gas (3×). Potassium phosphate tribasic (104 mg, 0.489 mmol) in Water (543 μl) (degassed) was then added to the reaction mixture. The reaction was allowed to stir at 60° C., for 1 hour. The reaction was then filtered through celite and loaded onto silica gel. The reaction mixture was purified by MPLC 0-50% EtOAc/DCM to give 6-chloro-3-methoxy-4-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine (49B). MS: [M+H]+ m/z 517.

Workup

  1. customThe mixture was evacuated
  2. additionback-filled with N2 gas (3×)
  3. filtrationThe reaction was then filtered through celite and
  4. customThe reaction mixture was purified by MPLC 0-50% EtOAc/DCM

Sources & evidence

ORD record
ord-9471ee66399d46c9b71ff00aab7f492d
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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