Sodium Carbonate → HCID 117667804, compound

HRID 712769Notes

Reaction equation

HRID 712769 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[CH2:17][CH2:16][N:15]([C:18]([NH2:20])=[O:19])[C:12]3=[N:13][CH:14]=2)O1.Br[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1[CH3:29].C([O-])([O-])=O.[Na+].[Na+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:29][C:28]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[C:9]1[CH:10]=[C:11]2[CH2:17][CH2:16][N:15]([C:18]([NH2:20])=[O:19])[C:12]2=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 8176303-Bromo-4-methylpyridineHCID 123704638HCID 123704638, compound

Product 1

HCID 117667804HCID 117667804, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
100 °C

Procedure

A crude solution of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carboxylic acid amide (0.41 mmol) is added to 3-bromo-4-methyl-pyridine (64 mg, 0.37 mmol) followed by the addition of aqueous 2.0 M Na2CO3 solution (0.41 mL, 0.82 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (420 mg, 0.52 mmol). The vial is sealed and the mixture is sparged with Ar (10 seconds). The reaction is stirred for 3 hours at 100° C. The reaction mixture is concentrated to dryness and dissolved in 2 mL of DMF, filtered and purified by reverse phase HPLC to afford the titled product.

Workup

  1. customThe vial is sealed
  2. customthe mixture is sparged with Ar (10 seconds)
  3. concentrationThe reaction mixture is concentrated to dryness
  4. dissolutiondissolved in 2 mL of DMF
  5. filtrationfiltered
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-57a11b73c96c4911867c97638d7ddb41
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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