Water → 9-(4-(5-bromopyridin-2-yl)phenyl)-9H-carbazole

HRID 521543Notes

Reaction equation

HRID 521543 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:21]4[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][CH:10]=2)O1.[Br:29][C:30]1[CH:31]=[CH:32][C:33](I)=[N:34][CH:35]=1.C([O-])([O-])=O.[Na+].[Na+].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.CCOC(C)=O.C1COCC1>[Br:29][C:30]1[CH:31]=[CH:32][C:33]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:22]4[C:27]3=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:11][CH:10]=2)=[N:34][CH:35]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5936905-Bromo-2-iodopyridineHCID 118500739-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

Product 1

HCID 667995889-(4-(5-bromopyridin-2-yl)phenyl)-9H-carbazoleYield 90.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure for 1, 5 (4.84 g, 13.1 mmol), 5-bromo-2-iodopyridine (3.72 g, 13.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.757 g, 0.655 mmol), Na2CO3 (4.97 g, 46.9 mmol), H2O (45 mL) and THF (75 mL) yielded 6 (4.73 g, 90% yield) as a colorless solid after flash chromatography (SiO2, 1:1 hexanes-dichloromethane) and subsequent trituration with EtOAc.

Sources & evidence

ORD record
ord-512497ae01d949749bdab547762fe399
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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