Sodium Bicarbonate → tert-butyl 4-(4-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d][1,2,3]triazol-6-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 871102Notes

Reaction equation

HRID 871102 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([S:31]([C:34]4[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=4)(=[O:33])=[O:32])[C:16]([C:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=4)=[CH:17][C:10]=23)O1.Br[C:43]1[CH:44]=[CH:45][C:46]2[N:50]=[N:49][N:48]([CH2:51][CH:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)[C:47]=2[CH:58]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.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].C(Cl)Cl>[O:55]1[CH2:56][CH2:57][CH:52]([CH2:51][N:48]2[C:47]3[CH:58]=[C:43]([C:9]4[CH:14]=[CH:13][N:12]=[C:11]5[N:15]([S:31]([C:34]6[CH:35]=[CH:36][C:37]([CH3:38])=[CH:39][CH:40]=6)(=[O:33])=[O:32])[C:16]([C:18]6[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=6)=[CH:17][C:10]=45)[CH:44]=[CH:45][C:46]=3[N:50]=[N:49]2)[CH2:53][CH2:54]1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 90407953HCID 90407953, compoundHCID 90408034HCID 90408034, compound

Product 1

HCID 90409594tert-butyl 4-(4-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d][1,2,3]triazol-6-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 36D (0.800 g, 1.380 mmol), 6-bromo-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d][1,2,3]triazole (0.450 g, 1.519 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.045 g, 0.055 mmol), and aqueous sodium bicarbonate (6 mL, 1.380 mmol) in N,N-dimethylformamide (20 mL) was degassed and the mixture was heated at 80° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous NaHCO3/brine and water, dried over MgSO4, filtered, and purified on a 40 g column using the ISCO Companion flash system eluting with heptanes/ethyl acetate (4:6 to 3:7) to give the title compound.

Workup

  1. washwashed with aqueous NaHCO3/brine and water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. custompurified on a 40 g column
  5. washeluting with heptanes/ethyl acetate (4:6 to 3:7)

Sources & evidence

ORD record
ord-2968607ad7a0416dac27fefaed981109
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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