Methyl iodide → HCID 59769884, compound

HRID 2218749Notes

Reaction equation

HRID 2218749 reaction equation
[CH2:1]=[C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[N:6]=[CH:5][S:4][C:3]1=2.N1C2CCC3C=CC=CC=3C(=O)C=2S[CH:17]=1.IC>C1COCC1>[CH3:17][C:5]1[S:4][C:3]2[C:2](=[CH2:1])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][CH2:8][C:7]=2[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 57736578HCID 57736578, compoundHCID 68938345HCID 68938345, compound

Product 1

HCID 59769884HCID 59769884, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add 1.2 equiv of n-BuLi-hexanes dropwise to a solution of 4-methylene-9,10-dihydro-4H-3-thia-1-aza-benzo[f]azulene (prepared from 9,10-dihydro-3-thia-1-aza-benzo[f]azulen-4-one (see Scheme XIII(b) as in Preparation 23) in THF (0.08 M) at −78° C. under Ar. Stir the resultant dark green solution for 5 min before adding 1.2 equiv of iodomethane in THF. Allow to warm and stir at room temperature for 18 h before quenching with excess water. Separate layers and extract the aqueous layer with diethyl ether (3×) and then dry (MgSO4) and concentrate the combined organic layers under reduced pressure. Use in the next step without further purification: 1H NMR (CDCl3, 400 MHz) δ 2.60 (s, 3 H), 3.03-3.13 (m, 4 H), 5.34 (s, 1 H), 5.53 (s, 1 H), 7.20-7.28 (m, 3 H), 7.33 (m, J=7.2 Hz, 1 H). TLC Rf=0.30 (10% EtOAc:hexanes).

Workup

  1. temperatureto warm
  2. stirringstir at room temperature for 18 h
  3. custombefore quenching with excess water
  4. extractionSeparate layers and extract the aqueous layer with diethyl ether (3×)
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate the combined organic layers under reduced pressure
  7. customUse in the next step without further purification

Sources & evidence

ORD record
ord-9741f5af5d83434cbff0e395e22c0388
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

Loading…