Diphenylamine → HCID 69000985, compound

HRID 2099955Notes

Reaction equation

HRID 2099955 reaction equation
BrC1C=C2C([C:6]3[CH:7]=[CH:8][C:9]([C:19]4[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=4)=[CH:10][C:11]=3[C:12]2([CH2:17][CH3:18])[CH2:15][CH3:16])=CC=1.[C:25]1([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C[C:39]([CH3:42])([O-])[CH3:40].[Na+].[C:44](P(C(C)(C)C)C(C)(C)C)(C)([CH3:46])[CH3:45]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O.C1(C)C=CC=CC=1>[CH2:17]([C:12]1([CH2:15][CH3:16])[C:34]2[CH:33]=[C:32]([N:31]([C:40]3[CH:39]=[CH:42][CH:46]=[CH:44][CH:45]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:37]=[CH:36][C:35]=2[C:6]2[C:11]1=[CH:10][C:9]([C:19]1[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=1)=[CH:8][CH:7]=2)[CH3:18]

Participants

8

Reactant 4

HCID 11487DiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 57796676HCID 57796676, compound

Product 1

HCID 69000985HCID 69000985, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3.00 parts of 2-(7-bromo-9,9-diethyl-9H-fluoren-2-yl)-1-methyl-1H-pyrrole (22), 1.54 parts of diphenylamine, 1.14 parts of sodium tert-butoxide, 0.09 parts of Pd(dba)2, and 0.065 parts of tri-tert-butyl phosphine were added into 50 parts of toluene under stirring to obtain a mixture. Then, the mixture was heated to 80° C. and reacted for 8 hours. After the reaction was stopped by water, a product was extracted by diethyl ether, and then dehydrated by magnesium sulfate. After the solvent was removed, the product was purified by dichloromethane/hexane in a silica gel column to obtain the compound (23a) of the present example.

Workup

  1. customto obtain a mixture
  2. customreacted for 8 hours
  3. extractiona product was extracted by diethyl ether
  4. customAfter the solvent was removed
  5. customthe product was purified by dichloromethane/hexane in a silica gel column

Sources & evidence

ORD record
ord-7d52e207622542d4bdcae275614728fc
Source dataset
uspto-grants-2009_08
Patent number
US07569704B1

Reaction notes

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