Sodium Carbonate → HCID 70267344, compound

HRID 1871165Notes

Reaction equation

HRID 1871165 reaction equation
[C:1]1([N:7]([C:14]2[CH:26]=[CH:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:16]=3[C:15]=2Br)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C(O)C>[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[C:1]1[CH:6]=[CH:5][C:4]([C:20]2[CH:19]=[C:18]3[C:23]([C:24]4[CH:25]=[CH:26][C:14]([N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)=[CH:15][C:16]=4[C:17]3([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:22][CH:21]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 18694822HCID 18694822, compoundHCID 223525161,3-Benzothiazol-2-ylboronic acid

Product 1

HCID 70267344HCID 70267344, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
87.5 °C

Procedure

A mixture of diphenylamino-9,9-diethyl-bromofluorene (7.02g, 0.015 mol), benzothiazole boronic acid (7.5 g 0.029 mol.), ethanol (50 ml), in NMP (50 ml) was degassed by bubbling nitrogen through the solution for 20 min. Sodium carbonate (13.0 g, 0.12 mol.) and 5% palladium on charcoal (1.5 g ) were then added, the mixture heated at 85-90° C. for 42 hrs. The resulting solids (18.0 g) that separated upon cooling were collected, washed with ethanol and dried. The solids were then transferred to a chromatograph column containing 300 g of alumina. Elution with 1:1 toluene-heptane gave the product, 4.98 g. (55.5% yield), m.p. 243.6-246.1° C. Recrystallization from toluene did not raise the melting point. Mass Spec: m/z 598, (M+). Analysis calculated for C42H34N2S: C, 84.25; H, 5.72; N, 4.68; S, 5.34. Found: C, 83.87; H, 6.02; N, 5.04; S, 5.29.

Workup

  1. customin NMP (50 ml) was degassed
  2. customby bubbling nitrogen through the solution for 20 min
  3. customThe resulting solids (18.0 g) that separated
  4. temperatureupon cooling
  5. customwere collected
  6. washwashed with ethanol
  7. customdried
  8. additioncontaining 300 g of alumina
  9. washElution with 1:1 toluene-heptane
  10. customgave the product, 4.98 g
  11. customRecrystallization from toluene
  12. temperaturedid not raise the melting point

Sources & evidence

ORD record
ord-fe6d77122f2847db9daddfcc8daa2df4
Source dataset
uspto-grants-2000_08
Patent number
US06100405

Reaction notes

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