Ethanol → HCID 178505617, compound

HRID 1875459Notes

Reaction equation

HRID 1875459 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]#[N:15])[N:6]=1.C([Sn](=O)CCCC)CCC.C[Si]([N:34]=[N+:35]=[N-:36])(C)C.C(O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]2[NH:36][N:35]=[N:34][N:15]=2)[N:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 591778713-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carbonitrile

Product 1

HCID 178505617HCID 178505617, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 188 mg (0.75 mmol) of 3-(2-fluorobenzyl)imidazo[1,5-a]pyridine-1-carbonitrile from example 18A, 18.6 mg (0.075 mmol) of dibutyltin oxide and 172 mg (1.50 mmol) of trimethylsilyl azide in 5 ml of toluene is heated under reflux for 20 h. Cooling is followed by addition of 5 ml of ethanol and stirring at RT for 15 h. The mixture is then concentrated, mixed with water and extracted with ethyl acetate. The organic phase is concentrated in vacuo, and the residue is purified by preparative HPLC. The product is taken up in ethyl acetate and clarified with activated carbon. The solid obtained after concentration is crystallized from dichloromethane. 40 mg (18% of theory) of the title compound are obtained as pale reddish crystals.

Workup

  1. temperatureunder reflux for 20 h
  2. temperatureCooling
  3. concentrationThe mixture is then concentrated
  4. additionmixed with water
  5. extractionextracted with ethyl acetate
  6. concentrationThe organic phase is concentrated in vacuo
  7. customthe residue is purified by preparative HPLC
  8. customThe solid obtained
  9. concentrationafter concentration
  10. customis crystallized from dichloromethane

Sources & evidence

ORD record
ord-8f7602c6565d48768c1a3f4719b11a15
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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