Dichloromethane → HCID 89963624, compound

HRID 1052257Notes

Reaction equation

HRID 1052257 reaction equation
Br[C:2]1[N:22]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:5]2=[N:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=3)[N:9]=[C:4]2[CH:3]=1.C(OC([N:39]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[N:40]1)=O)(C)(C)C.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.O1CCOCC1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][C:8]2[N:9]=[C:4]3[CH:3]=[C:2]([C:42]4[CH:43]=[N:39][NH:40][CH:41]=4)[N:22]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[C:5]3=[N:6][CH:7]=2)[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 899637236-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 89963624HCID 89963624, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
88 °C

Procedure

A stirred mixture of 6-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (180 mg, 0.358 mmol), tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (106 mg, 0.360 mmol), [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (29.2 mg, 0.0358 mmol), and potassium phosphate (153 mg, 0.719 mmol) in water (2 mL)/1,4-dioxane (5 mL) was heated at 88° C. After 1 hour, the reaction mixture was cooled to ambient temperature, quenched with water, and extracted with methylene chloride. The combined organic layers were dried over MgSO4, and then concentrated. The residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes) to give the desired product (132 mg, 75%). LCMS calculated for C25H24N5O4S (M+H)+: m/z=490.2. Found: 490.2.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7968057d543a4e2a807d2a2b0fc166f8
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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