Tert-Butyl isocyanide → HCID 90159433, compound

HRID 1054337Notes

Reaction equation

HRID 1054337 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH:9]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15])=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>[C:33]([NH:31][C:32]1[N:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[N:8][C:9]=1[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15])([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 90670m-FormylbenzonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 90159433HCID 90159433, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-fluoropyridin-2-amine (200 mg, 1.78 mmol, Eq: 1.00), 3-formylbenzonitrile (246 mg, 1.87 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (102 mg, 535 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 (148 mg, 203 μL, 1.78 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 1 h whereupon a white precipitate was formed. The precipitate was filtered off, washed with MeOH (4 mL) and dried under vacuum to give the product as an off-white solid (323 mg, 58.7%). MS: 308.0 [M]+; 1H-NMR (CDCl3): δ 8.35 (s, 1H), 8.26 (d, 1H), 8.14 (m, 1H), 7.63 (d, 1H), 7.60-7.52 (m, 2H), 7.13 (ddd, 1H), 3.01 (s, 1H), 1.10 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-e8cad69ba63f400ab00c8b0cc4adbd7c
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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