Tert-Butyl isocyanide → HCID 74220977, compound

HRID 1054331Notes

Reaction equation

HRID 1054331 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]([C:36]([CH3:39])([CH3:38])[CH3:37])#[C-:35]>CO.O>[C:36]([NH:34][C:35]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:17]=1[C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([C:12]#[CH:13])[CH:15]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 27716443-Ethynylbenzaldehyde

Product 1

HCID 74220977HCID 74220977, compoundYield 54.4%

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-isocyano-2-methylpropane (51.3 mg, 70.2 μL, 617 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. Water was added, the oil was separated from water/MeOH phase and purified by flash column chromatography (40 g SiO2, Hex/EtOAc 100:0 to 0:100) to yield a yellow solid (120 mg, 54.4%). MS: 357.0 [M]+; 1H-NMR (D6-DMSO): δ 8.89 (s, 1H), 8.38 (s, 1H), 8.27 (d, 1H), 7.72 (d, 1H), 7.52-7.40 (m, 3H), 4.94 (s, 1H), 4.22 (s, 1H), 1.04 (s, 9H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. customthe oil was separated from water/MeOH phase
  3. custompurified by flash column chromatography (40 g SiO2, Hex/EtOAc 100:0 to 0:100)

Sources & evidence

ORD record
ord-7efbfab24c6a487ea700cf6d7724e060
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

Loading…