Tert-Butyl isocyanide → HCID 74763780, compound

HRID 1054323Notes

Reaction equation

HRID 1054323 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.[F: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>[C:35]([NH:33][C:34]1[N:7]2[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=[CH:5][C:6]2=[N:9][C:16]=1[C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 680093-FluorobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 74763780HCID 74763780, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol, Eq: 1.00), 3-fluorobenzaldehyde (161 mg, 137 μl, 1.3 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (70.4 mg, 370 μmol, Eq: 0.3) were dissolved in MeOH (2.00 mL) and the intensive yellow solution was stirred for 20 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (103 mg, 140 μl, 1.23 mmol, Eq: 1.00) and the corresponding light yellow solution was stirred for 90 min. The solvent was removed, the remaining solid was treated with MeOH, the precipitate was filtered off, washed with MeOH (2 mL) and dried under vacuum to give the product as a white solid (42 mg, 9.7%). MS: 352.2 [M+H]+; 1H-NMR (CDCl3): δ 8.53 (s, 1H), 7.67-7.53 (m, 3H), 7.35 (m, 1H), 7.24 (dd, 1H), 6.98 (ddd, 1H), 3.06 (s, 1H), 1.01 (s, 9H).

Workup

  1. stirringthe corresponding light yellow solution was stirred for 90 min
  2. customThe solvent was removed
  3. additionthe remaining solid was treated with MeOH
  4. filtrationthe precipitate was filtered off
  5. washwashed with MeOH (2 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b78e11e7ae284c7d98336547631be5cc
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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