Sodium Bicarbonate → HCID 136341363, compound

HRID 1776810Notes

Reaction equation

HRID 1776810 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[Cl:27][C:28]1[N:33]=[C:32](I)[C:31]([OH:35])=[CH:30][CH:29]=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:27][C:28]1[N:33]=[C:32]([C:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:16]3[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH:10]=2)[C:31]([OH:35])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 234331586-Chloro-2-iodo-3-hydroxypyridineHCID 57562462HCID 57562462, compound

Product 1

HCID 136341363HCID 136341363, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a degassed solution of (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid (500 mg, 1.17 mmol), NaHCO3 (287 mg, 3.42 mmol) and 6-chloro-2-iodopyridin-3-ol (525 mg, 2.05 mmol) in 1,4-dioxane (10 mL) was added Pd(dppf)Cl2 (10 mg) under N2. The mixture was heated at 70° C. for 5 hours, concentrated in vacuo to remove 1,4-dioxane and extracted with EtOAc. After washed with brine and dried over Na2SO4, the solvent was removed by distillation. After concentrated, the crude product of tert-butyl 2-(6-chloro-3-hydroxypyridin-2-yl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (260 mg, yield: 40%). MS (M+H)+: 376/378.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove 1,4-dioxane
  3. extractionextracted with EtOAc
  4. washAfter washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed by distillation
  7. concentrationAfter concentrated

Sources & evidence

ORD record
ord-2e22e5d338cb4c138fb5a48f1dfb3e40
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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