Carbazole → HCID 86723549, compound

HRID 2206819Notes

Reaction equation

HRID 2206819 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[C:15]1[CH:16]=[CH:17][C:18]2[S:22][CH:21]=[C:20]([N:23]3[C:35]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:29]4[C:24]3=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:19]=2[CH:36]=1>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.O1CCCC1>[S:22]1[CH:21]=[C:20]([N:23]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:19]2[CH:36]=[C:15]([N:12]3[C:13]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:16]=[CH:17][C:18]1=2

Participants

5

Reactant 2

HCID 6854CarbazoleHCID 86723548HCID 86723548, compound

Product 1

HCID 86723549HCID 86723549, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In a 250 mL 2-neck round flask, 5 mL of tetrahydrofuran (THF) was poured to carbazole (0.75 g, 4.5 mmol). Then, a 2.5Mn-butyllithium/hexane solution (1.8 ml) was gradually added to the mixture in an ice bath. This mixture solution was stirred at room temperature for minutes, and then 9-(5-chlorobenzothiophen-3-yl)carbazole (1.5 g, 4.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (Pd(pph3)4) (0.024 g) were poured to the mixture solution, the resulting mixture was dissolved in and tetrahydrofuran, and reacted at 80° C. After the reaction, the precipitate was filtered and recrystallized with dichloromethane and methanol, thereby giving 1.71 g of a product (82%).

Workup

  1. customreacted at 80° C
  2. customAfter the reaction
  3. filtrationthe precipitate was filtered
  4. customrecrystallized with dichloromethane and methanol

Sources & evidence

ORD record
ord-14a01f8ec3784c519ab338c19675b00d
Source dataset
uspto-grants-2016_06
Patent number
US09373794B2

Reaction notes

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