Water → HCID 86722501, compound

HRID 516488Notes

Reaction equation

HRID 516488 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[C:31]([C:36]2[CH:41]=[CH:40][C:39]([C:42]3[N:46]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:45]4[CH:53]=[CH:54][CH:55]=[CH:56][C:44]=4[N:43]=3)=[CH:38][CH:37]=2)=[CH:32][CH:33]=[CH: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.O1CCOCC1>[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[C:31]([C:36]5[CH:41]=[CH:40][C:39]([C:42]6[N:46]([C:47]7[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=7)[C:45]7[CH:53]=[CH:54][CH:55]=[CH:56][C:44]=7[N:43]=6)=[CH:38][CH:37]=5)=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 513584509-Phenyl-9H-carbazole-3-boronic acidHCID 86722500HCID 86722500, compound

Product 1

HCID 86722501HCID 86722501, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following the procedure for Host-1, (9-phenyl-9H-carbazol-3-yl)boronic acid (0.458 g, 1.60 mmol), Compound 3 (0.800 g, 1.60 mmol), tetrakis(triphenylphosphine)palladium(0) (73.7 mg, 63.8 μmol), Na2CO3 (0.530 g, 5.00 mmol), H2O (5 mL) and 1,4-dioxane (25 mL) provided Host-2 (0.78 g, 74%) as an off-white solid after flash chromatography (SiO2, 17:3-hexanes: acetone) and recrystallization from methanol (CH3OH): confirmed by LCMS (APCI): calculated for C49H33N3 (M+): 664; Found: 664.

Workup

  1. customprovided Host-2 (0.78 g, 74%) as an off-white solid
  2. customafter flash chromatography (SiO2, 17:3-hexanes: acetone) and recrystallization from methanol (CH3OH)

Sources & evidence

ORD record
ord-4a495f18161f4b42812ebf5d1b82c21b
Source dataset
uspto-grants-2015_08
Patent number
US09112159B2

Reaction notes

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