Carbon Dioxide → HCID 90386893, compound

HRID 1424769Notes

Reaction equation

HRID 1424769 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36](Br)[CH:35]=1)[C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:27]4[C:22]3=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1.C(=O)=O.C([Li])CCC.Cl[Si:50](Cl)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CC(C)=O.C1COCC1>[CH:23]1[C:22]2[N:21]([C:17]3[CH:16]=[C:15]([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([N:8]5[C:3]6[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=6[Si:50]([C:57]6[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=6)([C:51]6[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=6)[C:35]6[CH:36]=[CH:37][CH:38]=[CH:39][C:34]5=6)[CH:10]=4)[CH:20]=[CH:19][CH:18]=3)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 6627DichlorodiphenylsilaneHCID 90387074HCID 90387074, compoundHCID 178418339Butyllithium

Product 1

HCID 90386893HCID 90386893, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

N-(2-bromophenyl)-N-(3-bromophenyl)-3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-amine was added into a 250 mL round bottom flask, and solubilized in dry THF (155 ml). The solution was cooled down to −78° C. using dry ice and Acetone. Butyllithium (7.45 ml, 18.62 mmol) was added dropwise and the reaction mixture was stirred −78° C. for 2 hours. Dichlorodiphenylsilane (2.108 ml, 10.24 mmol) was then added dropwise. The reaction mixture was allowed to slowly warm to room temperature and was stirred overnight. The reaction was quenched with water, extracted three times with ether, washed with brine and water. The crude material was purified with column chromatography using hexane/DCM (75/25). The product was collected as a white powder with a purity of 99.3% by HPLC. The product was recrystallized twice from DCM and hexane. The target 5-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-yl)-10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline (Compound 10) was afforded as a white powder (1.8 g, 29% yield). Compound 10 was then sublimed and 1.2 g was collected.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringwas stirred overnight
  3. customThe reaction was quenched with water
  4. extractionextracted three times with ether
  5. washwashed with brine and water
  6. customThe crude material was purified with column chromatography
  7. customThe product was collected as a white powder with a purity of 99.3% by HPLC
  8. customThe product was recrystallized twice from DCM and hexane

Sources & evidence

ORD record
ord-4e96fd46adb341b391dfb7ab2eff3cd1
Source dataset
uspto-grants-2015_01
Patent number
US08927749B2

Reaction notes

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