Potassium Carbonate → 1,1-dimethylethyl [2-({[2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate

HRID 1967101Notes

Reaction equation

HRID 1967101 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[C:4]([C:12]([NH:14][CH:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:13])[CH:3]=1.CC1(C)COB([C:39]2[N:43]([CH3:44])[N:42]=[CH:41][CH:40]=2)OC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[O:9]1[CH:10]=[CH:11][C:7]([C:5]2[S:6][C:2]([C:39]3[N:43]([CH3:44])[N:42]=[CH:41][CH:40]=3)=[CH:3][C:4]=2[C:12]([NH:14][CH:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:13])=[CH:8]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole2×HCID 581729311,1-Dimethylethyl [2-({[5-bromo-2-(3-furanyl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate

Product 1

HCID 581729091,1-dimethylethyl [2-({[2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl [2-({[5-bromo-2-(3-furanyl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate (140 mg, 0.277 mmol), 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (54 mg, 0.277 mmol), Pd(PPh3)4 (16 mg, 13.8 μmol) and K2CO3 (153 mg, 1.11 mmol) in dioxane (2.3 mL) and H2O (462 uL) were combined in a sealed tube. After 4 h at 80° C., additional 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (54 mg, 0.277 mmol) and Pd(PPh3)4 (16 mg, 13.8 μmol) were added. After an additional 12 h, the reaction contents were partitioned between H2O/DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and used directly: LCMS (ES) m/z=507 (M+H)+.

Workup

  1. waitAfter an additional 12 h
  2. customthe reaction contents
  3. customwere partitioned between H2O/DCM
  4. washThe aqueous phase was washed several times with DCM
  5. dry with materialthe combined organic fractions were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-772d796e1c7c4c5cb90c5f5a57fb8f35
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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