Sodium Carbonate → HCID 25165368, compound

HRID 1035480Notes

Reaction equation

HRID 1035480 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[C:15]([CH2:17][CH3:18])[N:14]=[C:13]([NH2:19])[N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C[C:21]1[C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][NH:23][N:22]=1.[C:35]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:17]([C:15]1[CH:16]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:25]4[CH:21]=[N:22][N:23]([CH3:35])[CH:24]=4)[CH:3]=3)[NH:8][CH:9]=2)[N:12]=[C:13]([NH2:19])[N:14]=1)[CH3:18]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 25164971HCID 25164971, compoundHCID 178434487HCID 178434487, compound

Product 1

HCID 25165368HCID 25165368, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 50 mg (0.157 mmol) of 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-ethylpyrimidin-2-ylamine, 56 mg (0.282 mmol) of methylpyrazole-4-boronic acid pinacol ester, 9 mg (0.008 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.45 ml of a 2M Na2CO3 solution (0.900 mmol) in 0.6 ml of DMF is heated for 30 min at 120° C. in the microwave. The reaction mixture is filtered, the filter cake is washed with MeOH, and the filtrate is evaporated in vacuo. The residue is purified by preparative HPLC, giving 4-ethyl-6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-ylamine as a colourless solid, ESI 320.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filter cake is washed with MeOH
  3. customthe filtrate is evaporated in vacuo
  4. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-9571e6a25e224d65b3895042cb8ba89a
Source dataset
uspto-grants-2013_10
Patent number
US08546390B2

Reaction notes

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