Sodium Bicarbonate → HCID 178451919, compound

HRID 1963979Notes

Reaction equation

HRID 1963979 reaction equation
C(=O)(O)[O-].[Na+].Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([C@@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[O:15][N:14]=2)=[CH:9][CH:8]=1.CC1(C)C(C)(C)OB([C:38]2[CH:43]=[CH:42][C:41]([C:44]3[NH:48][C:47]([C@@H:49]4[CH2:53][CH2:52][CH2:51][N:50]4[C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[N:46][CH:45]=3)=[CH:40][CH:39]=2)O1>COCCOC.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]>[C:26]([O:25][C:23]([N:19]1[CH2:20][CH2:21][CH2:22][C@H:18]1[C:16]1[O:15][N:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:38]3[CH:39]=[CH:40][C:41]([C:44]4[N:48]=[C:47]([C@@H:49]5[CH2:53][CH2:52][CH2:51][N:50]5[C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[NH:46][CH:45]=4)=[CH:42][CH:43]=3)=[CH:8][CH:9]=2)[N:17]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 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-carboxylate2×HCID 67224085HCID 67224085, compound2×

Product 1

HCID 178451919HCID 178451919, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A flask charged with PdCl2(dppf) (0.04 g, 0.051 mmol), sodium bicarbonate (0.37 g, 4.45 mmol), and (5)-tert-butyl 2-(3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate (compound 16a, 0.50 g, 1.27 mmol) was flushed with nitrogen. A solution of (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 (compound 20a, 0.67 g, 1.52 mmol) in 1,2-dimethoxyethane (15 ml) was then added. The reaction mixture was stirred at 80° C. under nitrogen for 6 hours. After cooled to room temperature, the resulting mixture was extracted with ethyl acetate/water, dried over magnesium sulfate, filtered and concentrated to give a crude compound, which was purified with chromatography (ethyl acetate: n-hexane=4:1) to yield product 23a as a white solid (0.57 g).

Workup

  1. customwas flushed with nitrogen
  2. temperatureAfter cooled to room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate/water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude compound, which
  8. customwas purified with chromatography (ethyl acetate: n-hexane=4:1)

Sources & evidence

ORD record
ord-350e7c4a27a04177b49e6e03b9948d84
Source dataset
uspto-grants-2013_04
Patent number
US08415482B2

Reaction notes

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