Sodium Bicarbonate → tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2'-chloro-3'-methyl-3,4'-bipyridine-2-carboxylate

HRID 1778932Notes

Reaction equation

HRID 1778932 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].C([O-])(O)=O.[Na+].[Cl:50][C:51]1[C:56]([CH3:57])=[C:55](I)[CH:54]=[CH:53][N:52]=1>O1CCOCC1.C(OCC)(=O)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>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C:26]([C:55]3[CH:54]=[CH:53][N:52]=[C:51]([Cl:50])[C:56]=3[CH3:57])=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 100836282-Chloro-4-iodo-3-methylpyridineHCID 89498009tert-butyl 6-(8-(benzo[d]thiazol2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate

Product 1

HCID 89498407tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2'-chloro-3'-methyl-3,4'-bipyridine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of EXAMPLE 30A (1.22 g) in dioxane (4 mL), and aqueous NaHCO3 (2 mL) was added 2-chloro-4-iodo-3-methylpyridine (505 mg), and tetrakis(triphenylphosphine)palladium(0) (115 mg). The mixture was stirred at 120° C. for 20 minutes in a Biotage Initiator microwave reactor. The mixture was diluted with ethyl acetate (300 mL) and washed with water (3 times) and brine, and dried over Na2SO4. Filtration and evaporation of the solvent gave crude product which was loaded on a silica gel column and eluted with 20% ethyl acetate in dichloromethane to provide the title compound.

Workup

  1. washwashed with water (3 times) and brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent
  4. customgave crude product which
  5. washeluted with 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-f31554bb1f8a4bd19727e88597d90e1c
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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