2-Chloro-4-nitroaniline → HCID 59304984, compound

HRID 2240241Notes

Reaction equation

HRID 2240241 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Cl:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH2:14].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(O)(C)(C)C>[Cl:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH:14][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 84922-Chloro-4-nitroanilineHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59304984HCID 59304984, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Variant B: A mixture of 200 mg (1.31 mmol) of 4-chloro-1H-pyrrolo[2,3-b]pyridine, 678 mg (3.93 mmol) of 2-chloro-4-nitroaniline, 60 mg (0.07 mmol) of tris(dibenzylideneacetone)dipalladium, 62 mg (0.13 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine and 399 mg (2.88 mmol) of potassium carbonate and 2.50 ml of degassed tert-butanol is stirred in a sealed pressure vessel at 100° C. for 3 h.

Sources & evidence

ORD record
ord-f42f7cfcb8d047c5b303fb7e3b54a553
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

Loading…