1-tert-butyloxycarbonyl-5,6-dimethoxy-1H-indole-3-boronic acid → 4-chloro-2-(5,6-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 490499Notes

Reaction equation

HRID 490499 reaction equation
[Cl:1][C:2]1[C:7](F)=[CH:6][N:5]=[C:4]2[N:9]([S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:10]([C:12]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[NH:14][CH:13]=3)=[CH:11][C:3]=12.C(OC(N1C2C(=CC(OC)=C(OC)C=2)C(B(O)O)=C1)=O)(C)(C)C>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:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:9]([S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:10]([C:12]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[NH:14][CH:13]=3)=[CH:11][C:3]=12

Participants

4

Reactant 2

HCID 671474461-tert-butyloxycarbonyl-5,6-dimethoxy-1H-indole-3-boronic acidHCID 671476144-Chloro-5-fluoro-2-(5,6-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 671474254-chloro-2-(5,6-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

4-Chloro-5-fluoro-2-(5,6-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine may be prepared by following the procedure described in Example 97c, but starting with 0.750 g of 1-(toluene-4-sulfonyl)-1H-2-iodo-4-chloro-5-fluoropyrrolo[2,3-b]pyridine, 0.534 g of 1-tert-butyloxycarbonyl-5,6-dimethoxyindol-3-boronic acid and 0.096 g of tetrakis(triphenylphosphine)palladium. 0.390 g of 4-chloro-2-(5,6-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is thus obtained, the characteristics of which are as follows:

Sources & evidence

ORD record
ord-483c4656dff842399930f94e5e1eeeca
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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