Potassium Carbonate → HCID 71698377, compound

HRID 539899Notes

Reaction equation

HRID 539899 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:12]=[C:11]([CH2:13][N:14]3[CH2:18][CH2:17][C@@H:16]([OH:19])[CH2:15]3)[C:10]([CH3:20])=[N:9]2)[CH:5]=[CH:4][N:3]=1.[Cl:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([NH2:31])[CH:29]=2)[N:24]([CH:32]2[CH2:34][CH2:33]2)[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[Cl:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([NH:31][C:2]3[N:7]=[C:6]([N:8]4[CH:12]=[C:11]([CH2:13][N:14]5[CH2:18][CH2:17][C@@H:16]([OH:19])[CH2:15]5)[C:10]([CH3:20])=[N:9]4)[CH:5]=[CH:4][N:3]=3)[CH:29]=2)[N:24]([CH:32]2[CH2:34][CH2:33]2)[CH:23]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86698989HCID 86698989, compoundHCID 86698990HCID 86698990, compound

Product 1

HCID 71698377HCID 71698377, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A round bottomed flask was charged with (R)-1-((1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methyl)pyrrolidin-3-ol (268 mg, 1.6 mmol), 3-chloro-1-cyclopropyl-1H-indol-5-amine (430 mg, 1.3 equiv.), potassium carbonate (0.66 g, 3.0 equiv), palladium acetate (18 mg, 0.05 equiv.), Xantphos (0.1 equiv.) and 50 mL of anhydrous dioxane. After being degassed by nitrogen bubbling, the reaction mixture was heated at 100° C. for 5 hours. Volatiles were removed in vacuo and then the resulting residue was extracted with dichloromethane. The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by silica gel chromatography (DCM/MeOH) to give 519 mg (70%) of the desired Compound 142 as a pale yellow solid. MS (ESI) m/z 464 [M+H]+.

Workup

  1. customAfter being degassed by nitrogen bubbling
  2. customVolatiles were removed in vacuo
  3. extractionthe resulting residue was extracted with dichloromethane
  4. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-bf2e1fa6198d4a0a91b97c1441b35306
Source dataset
uspto-grants-2014_10
Patent number
US08871778B2

Reaction notes

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