Potassium Carbonate → HCID 178451669, compound

HRID 417579Notes

Reaction equation

HRID 417579 reaction equation
I[C:2]1[S:3][C:4]2[C:12]([CH:13]=1)=[CH:11][C:10]1[S:9][C:8](I)=[CH:7][C:6]=1[CH:5]=2.[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][CH:23]1[C:27]1[NH:31][C:30]2[CH:32]=[CH:33][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:35][C:29]=2[N:28]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[C:45]([O-:48])([O-])=[O:46].[K+].[K+]>C1(C)C=CC=CC=1.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>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][CH:23]1[C:27]1[NH:28][C:29]2[CH:35]=[CH:34][C:33]([C:2]3[S:3][C:4]4[C:12]([CH:13]=3)=[CH:11][C:10]3[S:9][C:8]([C:34]5[CH:33]=[CH:32][C:30]6[NH:31][C:27]([CH:23]7[CH2:24][CH2:25][CH2:26][N:22]7[C:45]([O:48][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:46])=[N:28][C:29]=6[CH:35]=5)=[CH:7][C:6]=3[CH:5]=4)=[CH:32][C:30]=2[N:31]=1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 100720202,6-Diiodobenzo[1,2-b:4,5-b']dithiopheneHCID 178451668HCID 178451668, compound

Product 1

HCID 178451669HCID 178451669, compoundYield 36.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

2,6-Diiodo-1,5-dithia-s-indacene (117 mg, 0.263 mmol), 2-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-benzoimidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (109 mg, 0.263 mmol), Pd(PPh3)4 (9.1 mg), K2CO3 (69 mg, 0.52 mmol), were dissolved in toluene (5 mL)/water (1 mL) under an argon atmosphere. The mixture was heated for 30 minutes at 130° C. (microwave) and 30 minutes at 140° C. Removed all volatiles in vacuo and purified via silica gel chromatography (eluent: EtOAc/hexanes) to yield the product 2-(5-{6-[2-(1-Boc-pyrrolidin-2-yl)-1H-benzoimidazol-5-yl]-1,5-dithia-s-indacen-2-yl}-1H-benzoimidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (36.3 mg).

Workup

  1. customRemoved all volatiles in vacuo
  2. custompurified via silica gel chromatography (eluent: EtOAc/hexanes)

Sources & evidence

ORD record
ord-38c703fdcf334f8797dfe1810a506086
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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