Water → HCID 58400809, compound

HRID 1877717Notes

Reaction equation

HRID 1877717 reaction equation
Br[C:2]1[S:6][C:5]2[C:7]3[CH:11]=[C:10](Br)[S:9][C:8]=3[C:13]3[CH:17]=[C:16](Br)[S:15][C:14]=3[C:4]=2[CH:3]=1.[CH:19]1[C:31]2[N:30]([C:32]3[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.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>[CH:19]1[C:31]2[N:30]([C:32]3[CH:37]=[CH:36][C:35]([C:2]4[S:6][C:5]5[C:7]6[CH:11]=[C:10]([C:35]7[CH:34]=[CH:33][C:32]([N:30]8[C:29]9[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=9[C:23]9[C:31]8=[CH:19][CH:20]=[CH:21][CH:22]=9)=[CH:37][CH:36]=7)[S:9][C:8]=6[C:13]6[CH:17]=[C:16]([C:35]7[CH:36]=[CH:37][C:32]([N:30]8[C:29]9[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=9[C:23]9[C:31]8=[CH:19][CH:20]=[CH:21][CH:22]=9)=[CH:33][CH:34]=7)[S:15][C:14]=6[C:4]=5[CH:3]=4)=[CH:34][CH:33]=3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 231208274-(9H-Carbazol-9-yl)phenylboronic AcidHCID 58400797HCID 58400797, compound

Product 1

HCID 58400809HCID 58400809, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Under a nitrogen atmosphere, 2,5,8-tribromobenzo[1,2-b:3,4-b′:5,6-b″]trithiophene (33) (500 mg, 1.04 mmol) obtained in Example 4, 4-(N-carbazolyl)phenyl boronic acid (1.34 g, 4.66 mmol) and tripotassium phosphate hydrate (3.96 g, 18.6 mmol) were suspended in DMF (40 mL) and degassed by Ar bubbling for 30 minutes. Pd(PPh3)4 (179 mg, 0.155 mmol) was added and heated at 90-100° C. for 18 hours. After completion of the reaction, water (30 mL) was added. A precipitated solid substance was obtained by filtration, washed with water (50 mL) and acetone (10 mL) and dried under reduced pressure. Vacuum sublimation purification was performed to obtain a light yellow substance (47.7 mg, 5%). MS (MALDI-TOF,1,8,9-trihydroxyanthracene matrix) m/z=966.34

Workup

  1. customdegassed by Ar
  2. custombubbling for 30 minutes
  3. additionwas added
  4. customA precipitated solid substance was obtained by filtration
  5. washwashed with water (50 mL) and acetone (10 mL)
  6. customdried under reduced pressure
  7. customVacuum sublimation purification
  8. customto obtain a light yellow substance (47.7 mg, 5%)

Sources & evidence

ORD record
ord-98d4059c971d491c9e3f7db45ad19439
Source dataset
uspto-grants-2012_11
Patent number
US08313671B2

Reaction notes

Loading…