Sodium Carbonate → HCID 89525834, compound

HRID 571399Notes

Reaction equation

HRID 571399 reaction equation
Br[C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.[CH3:42][N:43]1[CH:47]=[CH:46][C:45](B2OC(C)(C)C(C)(C)O2)=[N:44]1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O1CCOCC1>[CH3:42][N:43]1[CH:47]=[CH:46][C:45]([C:2]2[C:6]3[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:16])=[O:13])=[CH:10][C:5]=3[N:4]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:3]=2)=[N:44]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27600771-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 89524439HCID 89524439, compound

Product 1

HCID 89525834HCID 89525834, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

(R)-1-(3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (36 mg, 0.060 mmol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (18.6 mg, 0.090 mmol), PdCl2(dppf)-CH2Cl2 adduct (7.3 mg, 8.96 μmol), 1,4-dioxane (0.6 mL) and Na2CO3 (0.08 mL, 0.160 mmol, 2M) were charged in a vial. The mixture was evacuated and purged with nitrogen six times and heated at 80° C. for 1 h. The mixture was diluted with EtOAc, washed with water, brine, dried (Na2SO4) and concentrated in vacuo to afford crude (R)-1-(3-(1-methyl-1H-pyrazol-3-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea, which was used as such in the next step. MS ESI calcd. For C38H34N7O [M+H]+ 604, found 604.

Workup

  1. customThe mixture was evacuated
  2. custompurged with nitrogen six times
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b1be244d21346e4b35ca7d0b0cf9e8c
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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