Potassium Carbonate → HCID 69675426, compound

HRID 1751405Notes

Reaction equation

HRID 1751405 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[NH:29][C:28]([C@@H:30]4[CH2:34][CH2:33][CH2:32][N:31]4[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[N:27][CH:26]=3)=[CH:21][CH:20]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O.C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:19]3[CH:20]=[CH:21][C:22]([C:25]4[NH:29][C:28]([C@@H:30]5[CH2:34][CH2:33][CH2:32][N:31]5[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[N:27][CH:26]=4)=[CH:23][CH:24]=3)[S:7][C:6]=2[CH:10]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 127444006-Bromo-benzo[b]thiopheneHCID 56605289(s)-tert-Butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1h-imidazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 69675426HCID 69675426, compoundYield 36.5%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-bromobenzo[b]thiophene (702 mg, 2.07 mmol), (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (700 mg, 1.59 mmol), tetrakis(triphenylphosphine) palladium (0) (184 mg, 0.15 mmol), potassium carbonate (440 mg, 3.19 mmol) in water (2 mL) and dimethoxyethane (10 mL) was heated in a microwave reactor at 130° C. for 30 minutes. The dimethoxyethane was removed under reduced pressure. The resulting residue was partitioned between water (15 mL) and dichloromethane (15 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (20 mL). The combined organic extracts were dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting residue was subjected to flash chromatography with eluant of (10% methanol in ethyl acetate) and hexane. The product containing fractions were combined and the solvent was removed under reduced pressure to provide (S)-tert-butyl 2-(5-(4-(6-bromobenzo[b]thiophen-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (302 mg, 0.58 mmol, 36%).

Workup

  1. customThe dimethoxyethane was removed under reduced pressure
  2. customThe resulting residue was partitioned between water (15 mL) and dichloromethane (15 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane (20 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. additionThe product containing fractions
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-06e115869a5b48108a1df8c21702d4ae
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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