Water → HCID 86711729, compound

HRID 2209337Notes

Reaction equation

HRID 2209337 reaction equation
BrC1C2[C:10](=CC=CC=2)[C:9]([C:16]2[CH:17]=[C:18]([C:22]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25]4[CH:33]=[CH:34][CH:35]=[CH:36][C:24]=4N=3)C=CC=2)=C2C=1C=CC=C2.[Br:37][C:38]1[C:39]2[C:44]([C:45](Br)=[C:46]3[C:51]=1[CH:50]=[CH:49][CH:48]=[CH:47]3)=[CH:43][CH:42]=[CH:41][CH:40]=2.C([O-])([O-])=O.[Na+].[Na+].O>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.C1COCC1>[Br:37][C:38]1[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45]([C:29]2[CH:28]=[C:27]([N:26]3[C:25]4[CH:24]=[CH:36][CH:35]=[CH:34][C:33]=4[C:10]4[C:22]3=[CH:18][CH:17]=[CH:16][CH:9]=4)[CH:32]=[CH:31][CH:30]=2)=[C:46]2[C:51]=1[CH:50]=[CH:49][CH:48]=[CH:47]2

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 682269,10-DibromoanthraceneHCID 58876089HCID 58876089, compound

Product 1

HCID 86711729HCID 86711729, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure as outlined above for synthesizing Compound 5, Compound (2.686 g, 7.274 mmol), 9,10-dibromoanthracene (7.333 g, 21.82 mmol), tetrakis(triphenylphosphine)palladium(0) (0.420 g, 0.364 mmol), Na2CO3 (9.539 g, 90.00 mmol), H2O (90 mL) and THF (150 mL) yielded Compound 8 (2.45 g, 68%) as a light yellow solid after flash chromatography (SiO2, 19:1 to 9:1 hexanes-dichloromethane).

Sources & evidence

ORD record
ord-55c6c852a9664050a724d5b740992b71
Source dataset
uspto-grants-2016_06
Patent number
US09379336B2

Reaction notes

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