Sodium Carbonate → HCID 86722504, compound

HRID 516490Notes

Reaction equation

HRID 516490 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17](C3N(C4C=CC=CC=4)C4C=CC=CC=4N=3)=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1.[C:35]1([N:41]2C3C=CC(B(O)O)=CC=3[C:47]3[C:42]2=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.BrC1C=CC=CC=1C1C=CC=CC=1Br.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.C(Cl)Cl.C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:35]3[C:36]([C:18]=2[CH:19]=1)=[CH:37][CH:38]=[CH:39][CH:40]=3

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 830602,2'-DibromobiphenylHCID 513584509-Phenyl-9H-carbazole-3-boronic acidHCID 86722500HCID 86722500, compound

Product 1

HCID 86722504HCID 86722504, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure for Compound 3, (9-phenyl-9H-carbazol-3-yl)boronic acid (1.84 g, 6.41 mmol), 2,2′-dibromo-1,1′-biphenyl (4.00 g, 12.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.296 g, 0.257 mmol), Na2CO3 (2.54 g, 24.0 mmol), H2O (24 mL) and THF (40 mL) yielded Compound 9 (1.69 g, 56%) as a colorless solid after flash chromatography (SiO2, 19:1-hexanes: CH2Cl2): confirmed by LCMS (APCI): calculated for C30H20NBr (M+): 474; Found: 474.

Sources & evidence

ORD record
ord-4c6e3eb5c46148ea815626c7d777b9dc
Source dataset
uspto-grants-2015_08
Patent number
US09112159B2

Reaction notes

Loading…