Ethanol → HCID 131735393, compound

HRID 630466Notes

Reaction equation

HRID 630466 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.C(O)C.Br[C:15]1[CH:16]=[N:17][C:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=3)[C:23]([S:34][CH3:35])=[CH:22]2)=[N:19][CH:20]=1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].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>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[N:19][C:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=3)[C:23]([S:34][CH3:35])=[CH:22]2)=[N:17][CH:16]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 27343542-Fluorophenylboronic acidHCID 118666039Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

Product 1

HCID 131735393HCID 131735393, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.13 mmol), 2-fluorophenylboronic acid (0.93 g, 6.64 mmol) and ethanol (40 mL) were added under an argon atmosphere to a mixture of 51b) (2.0 g, 5.3 mmol) in DME (40 mL) and 2M sodium carbonate solution (5.3 mL). The resulting mixture was heated at 90° C. for 3 h and then filtered through a pad of celite that was subsequently rinsed with dichloromethane (2×50 mL). The filtrate was concentrated and the remnant purified by column chromatography [100-200 mesh silica; dichloromethane/hexane=1:1]. White solid. Yield: 2.0 g (96% of theory). HPLC-MS (method 5): Rt=4.41 min; m/z [M+H]+=394

Workup

  1. filtrationfiltered through a pad of celite that
  2. washwas subsequently rinsed with dichloromethane (2×50 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe remnant purified by column chromatography [100-200 mesh silica; dichloromethane/hexane=1:1]

Sources & evidence

ORD record
ord-b23e21a5b82b462baf13810a155505e1
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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