Dichloromethane → HCID 73775239, compound

HRID 712077Notes

Reaction equation

HRID 712077 reaction equation
Br[C:2]1[C:3]([CH3:14])=[N:4][N:5]2[C:10]=1[C:9]1[S:11][CH:12]=[CH:13][C:8]=1[N:7]=[CH:6]2.[C:15]([CH2:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:16].C(=O)([O-])[O-].[Na+].[Na+].ClCCl>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].O.CN(C=O)C>[CH3:14][C:3]1[C:2]([C:21]2[CH:22]=[CH:23][C:18]([CH2:17][C:15]#[N:16])=[CH:19][CH:20]=2)=[C:10]2[N:5]([CH:6]=[N:7][C:8]3[CH:13]=[CH:12][S:11][C:9]=32)[N:4]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27733424-(Cyanomethyl)benzeneboronic acidHCID 86717534HCID 86717534, compound

Product 1

HCID 73775239HCID 73775239, compoundYield 64.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A microwave vial charged with 9-bromo-8-methylpyrazolo[1,5-c]thieno[2,3-e]pyrimidine (48.0 mg, 0.179 mmol), [4-(cyanomethyl)phenyl]boronic acid (from Aldrich, 51.9 mg, 0.322 mmol), sodium carbonate (47.4 mg, 0.448 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (15 mg, 0.018 mmol), DMF (1.3 mL) and water (0.13 mL) was purged with N2 and then stirred at 95° C. for 10 h. The reaction was diluted with ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude was purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product (35 mg, 64%). LCMS calculated for C17H13N4S (M+H)+: m/z=305.1. Found: 305.0.

Workup

  1. customwas purged with N2
  2. additionThe reaction was diluted with ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified with prep-LCMS (XBridge C18 column
  8. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-ab5bf405b53c4775837876f9a261fbd6
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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