3-Chlorobenzaldehyde → HCID 74762709, compound

HRID 1054329Notes

Reaction equation

HRID 1054329 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:31]([C:33]([CH3:36])([CH3:35])[CH3:34])#[C-:32]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]2[N:6]([C:32]([NH:31][C:33]([CH3:36])([CH3:35])[CH3:34])=[C:14]([C:13]3[CH:16]=[CH:17][CH:18]=[C:11]([Cl:10])[CH:12]=3)[N:8]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 23577Tert-Butyl isocyanideHCID 1379342-Amino-5-bromo-3-methylpyridineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 74762709HCID 74762709, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-bromo-3-methylpyridin-2-amine (200 mg, 1.07 mmol, Eq: 1.00), 3-chlorobenzaldehyde (158 mg, 128 μL, 1.12 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (61.0 mg, 321 μmol, Eq: 0.3) were dissolved in MeOH (1.5 mL) and the intensive yellow solution was stirred for 5 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (88.9 mg, 122 μL, 1.07 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. The precipitate was filtered off, washed with MeOH (4 mL) and dried under vacuum to give the product as a white solid (130 mg, 31.0%). MS: 394.1 [M+H]+; 1H-NMR (D6-DMSO): δ 8.48 (s, 1H), 8.27 (s, 1H), 8.17 (d, 1H), 7.46 (t, 1H), 7.36 (d, 1H), 7.22 (s, 1H), 4.81 (s, 1H), 3.34 (s, 3H), 1.03 (s, 9H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with MeOH (4 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-44781a896a9c4ef5a92f6bd699347192
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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