Nitrogen → HCID 68471318, compound

HRID 506780Notes

Reaction equation

HRID 506780 reaction equation
Br[C:2]1[C:6]2=[N:7][C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=[C:5]2[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]2[N:29]([S:45]([C:48]3[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=3)(=[O:47])=[O:46])[C:30]([Sn](CCCC)(CCCC)CCCC)=[CH:31][C:24]=12.N#N>C1(C)C=CC=CC=1.[Cu]I.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>[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]2[N:29]([S:45]([C:48]3[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=3)(=[O:47])=[O:46])[C:30]([C:2]3[C:6]4=[N:7][C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=[C:5]4[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=3)=[CH:31][C:24]=12

Participants

7

Reactant 3

HCID 947Nitrogen2×HCID 594326124-Chloro-1-(toluene-4-sulfonyl)-2-tributylstannanyl-1H-pyrrolo[2,3-b]pyridineHCID 68469784t-Butyl 3-bromo-5,6-dimethoxy-pyrrolo[3,2-b]pyridine-1-carboxylate

Product 1

HCID 68471318HCID 68471318, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Bubble a solution of dimethoxyazaindole 11 (0.25 g, 0.70 mmol) and azaindole 26 (0.458 g, 0.77 mmol) in toluene (15 mL) with N2 for 15 min, then add CuI (14 mg, 0.07 mmol) and Pd(PPh3)4 (81 mg, 0.07 mmol) and agitate the mixture with the stream of N2 for 0.5 h, then heat at 120° C. under N2 for 20 h. Purification of the reaction mixture on SiO2 (flash chromatography, 40 g cartridge, elution with EtOAc at 10-30%/heptane) gives bisazaindole 27 (0.28 g, 68%) as a white solid: 1H NMR (CDCl3) δ 8.29 (d, 1H, J=5.4 Hz), 7.86 (s apparent overlapping d, 3H), 7.15 (m, 4H), 6.94 (s, 1H), 3.97 (s, 6H), 2.32 (s, 3H), 1.71 (s, 9H), TLC (EtOAc at 40%/heptane) Rf=0.40.

Workup

  1. customPurification of the reaction mixture on SiO2 (flash chromatography, 40 g cartridge, elution with EtOAc at 10-30%/heptane)

Sources & evidence

ORD record
ord-42bc05642b8c4b2fadf73d196dd1e9ef
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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