Potassium Carbonate → HCID 178483613, compound

HRID 1888246Notes

Reaction equation

HRID 1888246 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])(=[O:22])=[O:21])[CH2:16][CH2:15]1.[F:29][C:30]([F:42])([F:41])[O:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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].BrC1C=C2C(=C(C(N)=O)C=1)NN=C2C1CCN(S(CCCN(C)C)(=O)=O)CC1>[CH3:27][N:26]([CH3:28])[CH2:25][CH2:24][CH2:23][S:20]([N:17]1[CH2:18][CH2:19][CH:14]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:35]4[CH:34]=[CH:33][C:32]([O:31][C:30]([F:29])([F:41])[F:42])=[CH:37][CH:36]=4)[CH:3]=3)[NH:7][N:6]=2)[CH2:15][CH2:16]1)(=[O:22])=[O:21]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 178483611HCID 178483611, compound

Product 1

HCID 178483613HCID 178483613, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178483611HCID 178483611, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution 5-bromo-3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indazole-7-carboxamide (Intermediate 8) (20 mg, 0.04 mmol) in dioxane/water (1:1, 5 mL) was added {4-[(trifluoromethyl)oxy]phenyl}boronic acid (30 mg, 0.12 mmol), potassium carbonate (40 mg), and Pd(dppf)Cl2 (8 mg). The reaction mixture was heated at 100° C. for 1800 seconds. The contents of the vial were partitioned between ethyl acetate and water. The organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give 0.62 g of a yellow solid. This was purified via silica gel chromatography using 20% ethyl acetate/pentane as the mobile phase to give the title compound (5 mg, 23%).

Workup

  1. customThe contents of the vial were partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-413a86d5bbd440df9ab22bb7ed3619e5
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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