Tert-Butyl isocyanide → HCID 74762783, compound

HRID 1054336Notes

Reaction equation

HRID 1054336 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:33]([C:35]([CH3:38])([CH3:37])[CH3:36])#[C-:34]>CO>[Br:12][C:13]1[CH:14]=[C:15]([C:16]2[N:9]=[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][N:7]3[C:34]=2[NH:33][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 765833-BromobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 74762783HCID 74762783, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(trifluoromethyl)pyridin-2-amine (0.5 g, 3.08 mmol, Eq: 1.00), 3-bromobenzaldehyde (599 mg, 378 μL, 3.24 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (176 mg, 925 μmol, Eq: 0.3) were dissolved in MeOH (4 mL) and the intensive yellow solution was stirred for 10 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (256 mg, 351 μL, 3.08 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 14 h. The solvent was removed and the crude product was purified by flash column chromatography (hexane/AcOEt 100/0 to 0/100) to yield a light yellow solid (865 mg, 68.0%). MS: 414.0 [M+H]+; 1H-NMR (D6-DMSO): δ 8.90 (s, 1H), 8.48 (s, 1H), 8.26 (d, 1H), 7.72 (d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 7.40 (t, 1H), 4.96 (s, 1H), 1.05 (s, 9H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 14 h
  2. customThe solvent was removed
  3. customthe crude product was purified by flash column chromatography (hexane/AcOEt 100/0 to 0/100)

Sources & evidence

ORD record
ord-31fe92d5301c4c89bef42421e84b6fd2
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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