HCID 25099315, compound → HCID 59200004, compound

HRID 2382114Notes

Reaction equation

HRID 2382114 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[NH:11][C:12]([C:14]1[C:15]([CH3:27])=[N:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[N:18][CH:19]=1)=[O:13]>C(Cl)Cl.O=[Mn]=O>[CH3:1][C:2]1[N:3]([NH:11][C:12]([C:14]2[C:15]([CH3:27])=[N:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[N:18][CH:19]=2)=[O:13])[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 25099315HCID 25099315, compound

Product 1

HCID 59200004HCID 59200004, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2-methyl-2,3-dihydro-indol-1-yl)-amide (246 mg, 0.68 mmol) and MnO2 (296 mg, 3.4 mmol) in DCM (10 mL) is stirred at rt for 1.5 h. The reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is triturated with ether to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2-methyl-indol-1-yl)-amide (158, 65%). MS: 361 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.39 (s, 3H), 2.83 (s, 3H), 6.36 (s, H), 7.10-7.29 (m, 3H), 7.44-7.62 (m, H), 8.17 (s, H), 8.25 (d, H), 8.35 (d, H), 8.97 (s, H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-23e393d0c66345079d1ceb1cbda7b16d
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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