N,N-Dimethylglycine → 3-(1-Methyl-1H-pyrazol-4-yl)-5-phenylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991102Notes

Reaction equation

HRID 1991102 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([C:16](C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:15]=3)=[CH:9][N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:5]2=[N:6][CH:7]=1.[C:43]1([SH:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CN(C)CC(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[CH3:16][N:14]1[CH:15]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([S:49][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:3]=3)[N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:40])[CH3:41])[CH:9]=2)[CH:12]=[N:13]1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 7969ThiophenolHCID 62657Potassium Phosphate, TribasicHCID 591286885-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 591865873-(1-Methyl-1H-pyrazol-4-yl)-5-phenylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 22 (50 mg, 0.079 mmol), benzenethiol (13.0 mg, 0.118 mmol), copper (I) iodide (3.0 mg, 0.016 mmol), N,N-dimethylglycine (1.62 mg, 0.016 mmol) and potassium phosphate (41.8 mg, 0.197 mmol) in DMF (0.5 mL) were heated at 120° C. for 69 h. The reaction mixture was cooled and partitioned between AcOEt/brine, the layers separated and the aqueous phase extracted with more AcOEt (2×). The combined organic extracts were dried (MgSO4) and concentrated. The resulting crude residue containing 23 was used for the subsequent deprotection step.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between AcOEt/brine
  3. customthe layers separated
  4. extractionthe aqueous phase extracted with more AcOEt (2×)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. additionThe resulting crude residue containing 23

Sources & evidence

ORD record
ord-5ecd8133a2d744029393622811a89cea
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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