Sodium Carbonate → HCID 59439660, compound

HRID 391506Notes

Reaction equation

HRID 391506 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:16]=[C:17]([CH:20]=[C:21](Br)[CH:22]=2)[CH:18]=[O:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.B1([C:32]2[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=2)OCC(C)(C)CO1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:16]=[C:17]([CH:20]=[C:21]([C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)[CH:22]=2)[CH:18]=[O:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27947173-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridineHCID 58480031HCID 58480031, compound

Product 1

HCID 59439660HCID 59439660, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

7.9 g (21.9 mmol) of 3-(anthracen-9-yl)-5-bromobenzaldehyde, 5 g (24.4 mmol of pyridine-3-boronic acid neopentylglycol ester, 0.85 g (3 mol %) of tetrakis(triphenylphosphine) palladium (0), and 5.17 g (48.8 mmol) of sodium carbonate were dissolved in 90 ml of tetrahydrofuran/H2O in a volume ratio of 2/1. The solution was reacted at 80° C. for 12 hours. The acquired reactant was extracted with ethyl acetate and treated under reduced pressure to remove the solvent. The extract was separated through a column, obtaining 7.24 g (Y=91%) of a white solid.

Workup

  1. customThe solution was reacted at 80° C. for 12 hours
  2. extractionThe acquired reactant was extracted with ethyl acetate
  3. additiontreated under reduced pressure
  4. customto remove the solvent
  5. customThe extract was separated through a column
  6. customobtaining 7.24 g (Y=91%) of a white solid

Sources & evidence

ORD record
ord-d2ab5fb476b243de89e5b9614ee0c95d
Source dataset
uspto-grants-2013_02
Patent number
US08383932B2

Reaction notes

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