Sodium Bicarbonate → HCID 86692085, compound

HRID 1469095Notes

Reaction equation

HRID 1469095 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]3[CH:29]=[CH:28][N:27]([Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[C:24]3=[N:25][CH:26]=2)O1.C(=O)([O-])O.[Na+]>O1CCOCC1.O.CC(=O)OCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([C:21]2[CH:22]=[C:23]3[CH:29]=[CH:28][N:27]([Si:30]([CH:34]([CH3:36])[CH3:35])([CH:37]([CH3:39])[CH3:38])[CH:31]([CH3:32])[CH3:33])[C:24]3=[N:25][CH:26]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 45480453Methyl 3-amino-6-bromopyridine-2-carboxylateHCID 45790150HCID 45790150, compound

Product 1

HCID 86692085HCID 86692085, compoundYield 65.5%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

7.50 g of methyl 3-amino-6-bromopyridine-2-carboxylate, 12.10 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-pyrrolo-[2,3-b]pyridine, 8.18 g of sodium hydrogencarbonate and 2.27 g of PdCl2(PPh3)2 in 90 ml of dioxane and 15 ml of water are heated at 90° C. under nitrogen in a flask until the reaction is complete (HPLC check, about 7 hours). The cooled reaction solution is diluted with EA and washed 3 times with water. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient heptane: EA 5-100% in 25 min), giving 8.40 g of methyl 3-amino-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridine-2-carboxylate as white solid (yield 56%, content 92%); MS-FAB (M+H+)=425.2; Rf (Esi1rod method): 3.10 min.

Workup

  1. custom(HPLC check, about 7 hours)
  2. customThe cooled reaction solution
  3. washwashed 3 times with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. custompurified by means of column chromatography (gradient heptane: EA 5-100% in 25 min)

Sources & evidence

ORD record
ord-f2cf2e366b9e4d4da4bcd5d907e7fd32
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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