Sodium Carbonate Decahydrate → HCID 66749464, compound

HRID 1405925Notes

Reaction equation

HRID 1405925 reaction equation
Br[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:17]2[CH:22]=[CH:21][C:20]([B:23]3[NH:28][C:27]4[CH:29]=[CH:30][CH:31]=[C:32]5[CH:33]=[CH:34][CH:35]=[C:25]([C:26]=45)[NH:24]3)=[CH:19][CH:18]=2)O1.O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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:24]1[C:25]2=[CH:35][CH:34]=[CH:33][C:32]3=[CH:31][CH:30]=[CH:29][C:27](=[C:26]23)[NH:28][B:23]1[C:20]1[CH:19]=[CH:18][C:17]([C:2]2[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 151402Sodium Carbonate DecahydrateHCID 8177002-Amino-3-bromopyridineHCID 24778108HCID 24778108, compound

Product 1

HCID 66749464HCID 66749464, compoundYield 47.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (57.7 mg) was added to a suspension of 3-bromopyridin-2-amine (432 mg), 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1016 mg) and sodium carbonate decahydrate (1429 mg) in DME (10 mL) and water (2 mL) and the mixture was stirred at 80° C. under nitrogen for 3 hr and at 70° C. overnight. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc). The filtrate was concentrated and the residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (397 mg) as a brown solid.

Workup

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-1fd07274d6b0423a9c323d562b4450a5
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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