Methyl iodide → Tert-butyl(6-amino-2-methoxypyridin-3-yl)methylcarbamate

HRID 1772907Notes

Reaction equation

HRID 1772907 reaction equation
C(OC(=O)N[C:8]1[C:9]([O:15][CH3:16])=[N:10][C:11](Br)=[CH:12][CH:13]=1)(C)(C)C.IC.CC(C)([O-])C.[Na+].C(=[NH:39])(C1C=CC=CC=1)C1C=CC=CC=1.[C:40]([O:44][C:45](=[O:57])[N:46](C1C(OC)=NC(Br)=CC=1)[CH3:47])([CH3:43])([CH3:42])[CH3:41]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:40]([O:44][C:45](=[O:57])[NH:46][CH2:47][C:8]1[C:9]([O:15][CH3:16])=[N:10][C:11]([NH2:39])=[CH:12][CH:13]=1)([CH3:43])([CH3:42])[CH3:41]

Participants

9

Reactant 5

HCID 6328Methyl iodideHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 118685238Tert-butyl(6-bromo-2-methoxypyridin-3-yl)(methyl)carbamateHCID 131734694tert-butyl N-(6-bromo-2-methoxypyridin-3-yl)carbamate

Product 1

HCID 131734695Tert-butyl(6-amino-2-methoxypyridin-3-yl)methylcarbamateYield 203.5%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared from tert-butyl(6-bromo-2-methoxypyridin-3-yl)carbamate (7.07 g, 23.3 mmol) and iodomethane (6.17 mL, 98.0 mmol); followed by sodium tert-butoxide (2.17 g, 22.6 mmol), BINAP (1.41 g, 2.26 mmol), benzophenone imine (2.08 mL, 12.4 mmol), tert-butyl(6-bromo-2-methoxypyridin-3-yl)(methyl)carbamate (3.58 g, 11.3 mmol) and Pd2(dba)3 (1.03 g, 1.13 mmol) in toluene (60 mL) at 80° C. using the methods of (IntA30), step 4. Combination with batches of material derived from tert-butyl(6-bromo-2-methoxypyridin-3-yl)(methyl)carbamate (3.24 g and 576 mg) before purification using the methods of (IntA30), step 4 yielded the title compound (5.83 g, 23.0 mmol).

Workup

  1. customCombination with batches of material derived from tert-butyl(6-bromo-2-methoxypyridin-3-yl)(methyl)carbamate (3.24 g and 576 mg) before purification

Sources & evidence

ORD record
ord-c6c1cb4022274cef9a29e604d24d193b
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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