1-Bromonaphthalene → HCID 9883637, compound

HRID 992000Notes

Reaction equation

HRID 992000 reaction equation
[C:1](=[N:14][NH2:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.CC([O-])(C)C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:25]1([NH:15][N:14]=[C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:26]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 70011-BromonaphthaleneHCID 79304DiphenylmethylidenehydrazineHCID 23676156Sodium t-butoxide

Product 1

HCID 9883637HCID 9883637, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent2×

Procedure

Benzophenone hydrazone (1 equiv., 10 mmol, 2.04 g), 1-bromonaphthalene (1.0 equiv., 10 mmol, 1.39 mL), Pd(OAc)2 (0.01 equiv., 0.1 mmol, 23 mg), BINAP (0.01 equiv., 0.1 mmol, 63 mg), and toluene (10 mL) were added to an oven dried Schlenk flask and stirred at room temperature for 2 minutes, NaOtBu (1.4 equiv., 14 mmol, 1.345 g) and an additional 10 mL of toluene were then added. The flask was capped with a septum and purged briefly with argon (˜1 min.) and heated to 80° C. under argon for 4.5 hours. The reaction mixture was then cooled to room temperature, diluted with Et2O (10 mL), and concentrated under vacuum to give the crude product as a brown solid. Recrystallization of the crude product from hot ethanol (150 mL) gave the desired product as a red solid (1.6939 g, 5.26 mmol, 53% yield). The mother liquor was concentrated until the solution became cloudy, and then heated until the solution became clear, filtered and cooled to −4° C. for 12 hours. The resulting crystals were filtered to give an additional 1.062 g of the title product as an orange/red solid (3.3 mmol, 33% yield), to give a 85% overall yield of the desired product.

Workup

  1. customdried Schlenk flask
  2. customThe flask was capped with a septum
  3. custompurged briefly with argon (˜1 min.)
  4. temperatureheated to 80° C. under argon for 4.5 hours
  5. temperatureThe reaction mixture was then cooled to room temperature
  6. additiondiluted with Et2O (10 mL)
  7. concentrationconcentrated under vacuum
  8. customto give the crude product as a brown solid
  9. customRecrystallization of the crude product from hot ethanol (150 mL)

Sources & evidence

ORD record
ord-06b022c39ea24e6380db71b83f6f2786
Source dataset
uspto-grants-2002_10
Patent number
US06465693B2

Reaction notes

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