Methanol → HCID 89815345, compound

HRID 525413Notes

Reaction equation

HRID 525413 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)O1.FC(F)(F)S(O[C:25]1[CH2:30][CH2:29][CH:28]([N:31]2[C@@H:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:34]([CH3:43])([CH3:42])[O:33][C:32]2=[O:44])[CH2:27][CH:26]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].CO>O1CCOCC1.C(Cl)Cl.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>[NH:15]1[C:12]2=[N:13][CH:14]=[C:9]([C:25]3[CH2:30][CH2:29][CH:28]([N:31]4[C@@H:35]([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:34]([CH3:42])([CH3:43])[O:33][C:32]4=[O:44])[CH2:27][CH:26]=3)[CH:10]=[C:11]2[CH:17]=[CH:16]1

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 89814036HCID 89814036, compound

Product 1

HCID 89815345HCID 89815345, compoundYield 100.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1 h-pyrrolo[2,3-b]pyridine (0.477 g, 1.955 mmol), 4-((S)-5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate (0.82 g, 1.955 mmol) and 2.0 M sodium carbonate (4.89 mL) in dioxane (6.52 mL) was flushed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.226 g, 0.196 mmol) was added and the mixture was stirred at 100° C. overnight. The reaction mixture was diluted with CH2Cl2 and extracted with CH2Cl2. The combined organic layers were concentrated. The material thus obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% 1M NH3.MeOH in CH2Cl2, to provide (4S)-3-(4-(1H-pyrrolo[2,3-b]pyridin-5-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.76 g, 1.961 mmol, 100% yield) as light-yellow solid.

Workup

  1. customwas flushed with nitrogen
  2. extractionextracted with CH2Cl2
  3. concentrationThe combined organic layers were concentrated
  4. customThe material thus obtained
  5. customwas absorbed onto a plug of silica gel
  6. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (40 g)
  7. washeluting with a gradient of 0% to 50% 1M NH3

Sources & evidence

ORD record
ord-e7467537e1184e1ca8f8833452fe7fad
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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