Sodium Bicarbonate → HCID 67147642, compound

HRID 2426892Notes

Reaction equation

HRID 2426892 reaction equation
I[C:2]1[N:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.C(OC([N:28]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[CH:34][C:35]=2[O:37][CH3:38])[C:30](B(O)O)=[CH:29]1)=O)(C)(C)C.C(=O)([O-])O.[Na+].C1CCCCC1.C(OCC)(=O)C>CN(C)C=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>[CH3:40][O:39][C:33]1[CH:32]=[C:31]2[C:36](=[C:35]([O:37][CH3:38])[CH:34]=1)[NH:28][CH:29]=[C:30]2[C:2]1[N:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 21867204Cyclohexane ethylacetateHCID 22477267HCID 22477267, compoundHCID 67147593HCID 67147593, compound

Product 1

HCID 67147642HCID 67147642, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

But using 2.9 g of 2-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, 2.34 g of 1-tert-butyloxycarbonyl-5,7-dimethoxy-1H-indole-3-boronic acid and 19 ml of a saturated aqueous solution of sodium hydrogen carbonate in 63 ml of dimethylformamide, and 0.42 g of tetrakis(triphenylphosphine)palladium is added. After flash chromatography on a silica column [eluent: cyclohexane/ethyl acetate (70/30 by volume)], 0.26 g of 2-(5,7-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is thus obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. additionis added

Sources & evidence

ORD record
ord-d9382c7b59184eb8865785b1e6798df3
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

Loading…