Ethanol → HCID 57781022, compound

HRID 1011234Notes

Reaction equation

HRID 1011234 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:21]C)[C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)[N:8]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH:7]=[C:6]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][C:33]=1[CH3:43])=[O:29])[C:5]2=[O:44].C[Si](I)(C)C.C(O)C.N1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:21])[C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)[N:8]([CH2:23][C:24]([F:25])([F:26])[F:27])[CH:7]=[C:6]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:40])([F:41])[F:42])=[CH:34][C:33]=1[CH3:43])=[O:29])[C:5]2=[O:44]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 85247Trimethylsilyl iodideHCID 57781000HCID 57781000, compound

Product 1

HCID 57781022HCID 57781022, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg (0.237 mmol) of the compound of Example 47 are provided in 3 ml of dichloromethane, 943 μl of trimethylsilyliodide (6.63 mmol) are added and the mixture is stirred for 4 days at room temperature. In order to destroy the excess trimethylsilyliodide the reaction mixture is cooled to 0° C., and a mixture of 414 μl of Ethanol (7.1 mmol) and 575 μl of pyridine (7.1 mmol) is added. After 5 min the volatile components are removed on a rotary evaporator. The residue is stirred in 5 ml of a water-acetonitrile mixture (1:1) and the solid is collected by filtration. It is dried under high vacuum. 136 mg of the title compound are obtained (91% of theory).

Workup

  1. customIn order to destroy the excess trimethylsilyliodide the reaction mixture
  2. temperatureis cooled to 0° C.
  3. additionis added
  4. customAfter 5 min the volatile components are removed on a rotary evaporator
  5. stirringThe residue is stirred in 5 ml of a water-acetonitrile mixture (1:1)
  6. filtrationthe solid is collected by filtration
  7. customIt is dried under high vacuum

Sources & evidence

ORD record
ord-d319d6ccc113400f9b45d859d577c584
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

Loading…