Isopropyl isocyanide → HCID 90158619, compound

HRID 1054334Notes

Reaction equation

HRID 1054334 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.[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)#[CH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:34]([CH:36]([CH3:38])[CH3:37])#[C-:35]>CO.O>[C:12]([C:14]1[CH:15]=[C:16]([C:17]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:35]=2[NH:34][CH:36]([CH3:38])[CH3:37])[CH:19]=[CH:20][CH:21]=1)#[CH:13]

Participants

7

Reactant 4

HCID 150783Isopropyl isocyanideHCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 27716443-Ethynylbenzaldehyde

Product 1

HCID 90158619HCID 90158619, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-(trifluoromethyl)pyridin-2-amine (100 mg, 617 μmol, Eq: 1.00), 3-ethynylbenzaldehyde (84.3 mg, 648 μmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (35.2 mg, 185 μmol, Eq: 0.3) were dissolved in MeOH (1.00 mL) and the intensive yellow solution was stirred for 5 min. To this yellow solution was added dropwise 2-isocyanopropane (42.6 mg, 58.2 μL, 617 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. Upon addition of water a yellow precipitate was formed. The solid was filtered off, washed with MeOH/water (1:1) and dried under vacuum to yield the product as a yellow solid (153 mg, 72.2%). MS: 344.0 [M+H]+; 1H-NMR (D6-DMSO): δ 8.90 (s, 1H), 8.36 (s, 1H), 8.25 (d, 1H), 7.71 (d, 1H), 7.50 (t, 1H), 7.46-7.39 (m, 2H), 5.10 (d, 1H), 4.24 (s, 1H), 3.25 (m, 1H), 1.08 (d, 6H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. customwas formed
  3. filtrationThe solid was filtered off
  4. washwashed with MeOH/water (1:1)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-cf2a4458d6e74eb19982b922764ac7d6
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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