Ethyl Bromide → 2-(6-benzyloxy-3-pyridyl)-5-cyclopropyl-6-[ethyl(methylsulfonyl)amino]-N-methyl-indazole-3-carboxamide

HRID 1037570Notes

Reaction equation

HRID 1037570 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[C:23]([C:24]([NH:26][CH3:27])=[O:25])=[C:22]3[C:17]([CH:18]=[C:19]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:20]([CH:28]4[CH2:30][CH2:29]4)=[CH:21]3)=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:36](OC1N=CC(N)=CC=1)[C:37]1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].BrCC>C(#N)C>[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[C:23]([C:24]([NH:26][CH3:27])=[O:25])=[C:22]3[C:17]([CH:18]=[C:19]([N:31]([CH2:36][CH3:37])[S:32]([CH3:35])(=[O:33])=[O:34])[C:20]([CH:28]4[CH2:29][CH2:30]4)=[CH:21]3)=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 5632866-(benzyloxy)pyridin-3-amineHCID 692514042-(6-benzyloxy-3-pyridyl)-5-cyclopropyl-6-(methanesulfonamido)-N-methyl-indazole-3-carboxamide2×

Product 1

HCID 677753662-(6-benzyloxy-3-pyridyl)-5-cyclopropyl-6-[ethyl(methylsulfonyl)amino]-N-methyl-indazole-3-carboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-(6-benzyloxy-3-pyridyl)-5-cyclopropyl-6-(methanesulfonamido)-N-methyl-indazole-3-carboxamide (109) ESI-MS m/z calculated for [M+H]+: 492.1 was prepared according to procedure outlined in Method A using 6-benzyloxypyridin-3-amine instead of 4-bromoaniline. To a solution of compound (109) (120 mg, 0.24 mmol) in acetonitrile (10 mL) was added potassium carbonate (100 mg, 0.72 mmol) followed by bromoethane (0.09 mL, 1.2 mmol). The mixture was heated to 80° C. and stirred for 1.5 h. The mixture was cooled to RT and the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate (10 mL), washed with water (2 mL), brine (2 mL), dried (MgSO4) and concentrated in vacuo to afford 2-(6-benzyloxy-3-pyridyl)-5-cyclopropyl-6-[ethyl(methylsulfonyl)amino]-N-methyl-indazole-3-carboxamide (i) (100 mg, 80%). This material was used without purification.

Workup

  1. custom492.1 was prepared
  2. temperatureThe mixture was cooled to RT
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate (10 mL)
  5. washwashed with water (2 mL), brine (2 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26ed5893763044efacdc2bea760e9d57
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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