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Cesium carbonate → HCID 67286074, compound

HRID 1036606
Notes
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Reaction equation

HRID 1036606 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/B2OC(C)(C)C(C)(C)O2)[CH:11]=[CH:12][CH:13]=1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35]2[N:38]([CH3:48])[C:39]([C:41]3[CH:46]=[CH:45][N:44]=[C:43](I)[N:42]=3)=[CH:40][C:34]=2[C:33]1=[O:49])=[O:31])([CH3:28])([CH3:27])[CH3:26]>O1CCOCC1.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>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35]2[N:38]([CH3:48])[C:39]([C:41]3[CH:46]=[CH:45][N:44]=[C:43](/[CH:15]=[CH:14]/[C:10]4[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=4)[N:42]=3)=[CH:40][C:34]=2[C:33]1=[O:49])=[O:31])([CH3:28])([CH3:27])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 162181612-[(E)-2-(3-Chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86667879HCID 86667879, compound

Product 1

HCID 67286074HCID 67286074, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Cesium carbonate (0.143 g, 0.438 mmol), palladium tetrakis (0.051 g, 0.042 mmol) and 2-[(E)-2-(3-Chloro-phenyl)-vinyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.116 g, 0.440 mmol) were added to a solution of 2-(2-Iodo-pyrimidin-4-yl)-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (synthesised as reported in Example 9) (0.100 g, 0.22 mmol) in dioxane (5.0 ml) under argon atmosphere. Argon was bubbled for 5 minutes, the vial was closed and the reaction mixture was heated by microwave irradiation for 30 minute at 100° C. for two cycles. In order to affect completion, a refresh of the catalyst and the base and two more cycles at the microwaves were carried on. The solvent was removed under vacuum, the residue was taken into DCM (5.0 ml), which was washed with a saturated solution of NaHCO3 (1×5.0 ml), brine (1×5.0 ml), and it was dried over Na2SO4. The filtrate was evaporated to dryness to give the crude product, which was purified by flash chromatography, over silica gel, using DCM/MeOH (9.9:0.1) as eluent, to afford 2-{2-[(E)-2-(3-Chloro-phenyl)-vinyl]-pyrimidin-4-yl}-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester yellow solid (0.051 g, 0.110 mmol, 50%).

Workup

  1. customArgon was bubbled for 5 minutes
  2. customthe vial was closed
  3. customThe solvent was removed under vacuum
  4. washwas washed with a saturated solution of NaHCO3 (1×5.0 ml), brine (1×5.0 ml), and it
  5. dry with materialwas dried over Na2SO4
  6. customThe filtrate was evaporated to dryness
  7. customto give the crude product, which
  8. customwas purified by flash chromatography, over silica gel

Sources & evidence

ORD record
ord-ece9979e4eaf4a6694151509641955d8
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546413B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes