Potassium Carbonate → HCID 86712054, compound

HRID 1755526Notes

Reaction equation

HRID 1755526 reaction equation
[CH3:1][C:2]1([CH3:39])[C:14]2[CH:13]=[C:12]([N:15]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5](B1OC(C)(C)C(C)(C)O1)=[CH:6][CH:7]=2.I[C:41]1[CH:46]=[CH:45][C:44]([Br:47])=[CH:43][N:42]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[Br:47][C:44]1[CH:45]=[CH:46][C:41]([C:5]2[CH:4]=[C:3]3[C:8]([C:9]4[CH:10]=[CH:11][C:12]([N:15]([C:23]5[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=5)[C:16]5[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=5)=[CH:13][C:14]=4[C:2]3([CH3:1])[CH3:39])=[CH:7][CH:6]=2)=[N:42][CH:43]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5936905-Bromo-2-iodopyridineHCID 86712055HCID 86712055, compound2×

Product 1

HCID 86712054HCID 86712054, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N,N-di-p-tolyl-9H-fluoren-2-amine (Compound 33) (5.0 g, 9.7 mmol), 2-iodo-5-bromo-pyridine (8.26 g, 29.1 mmol), Pd(PPh3)4 (0.56 g, 0.48 mmol) and K2CO3 (5.36 g, 38.8 mmol) in dioxane/water (65 mL/13 mL) was degassed and heated at about 90° C. overnight. The resulting mixture was worked up with ethyl acetate and brine. The organic phase was dried over Na2SO4, loaded on silica gel, purified by flash column (hexanes/dichloromethane 5:1 to 1:3 to dichloromethane). The desired fraction was collected, concentrated and recrystallized in dichloromethane/hexanes to give a white solid (Compound 34) (4.085 g, in 77% yield).

Workup

  1. customwas degassed
  2. dry with materialThe organic phase was dried over Na2SO4
  3. custompurified by flash column (hexanes/dichloromethane 5:1 to 1:3 to dichloromethane)
  4. customThe desired fraction was collected
  5. concentrationconcentrated
  6. customrecrystallized in dichloromethane/hexanes

Sources & evidence

ORD record
ord-73351cd7a824428da8ab5bbef8028f48
Source dataset
uspto-grants-2015_10
Patent number
US09172051B2

Reaction notes

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