Sodium Iodide → HCID 58677658, compound

HRID 1012642Notes

Reaction equation

HRID 1012642 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:18]=3[CH3:24])=[O:16])=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=2)=[C:4]([CH3:28])[CH:3]=1.Cl[CH2:30][CH2:31][CH2:32][OH:33].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[C:21]([O:23][CH2:30][CH2:31][CH2:32][OH:33])[CH:20]=[CH:19][C:18]=3[CH3:24])=[O:16])=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=2)=[C:4]([CH3:28])[CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 67313368HCID 67313368, compound

Product 1

HCID 58677658HCID 58677658, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Compound 505 (0.05 g, 0.13 mmol) and 3-chloro-propanol (0.022 mL, 0.26 mmol) were dissolved in CH3CN (3 mL). K2CO3 (0.1 g, 0.72 mmol) and NaI (0.005 g, 0.03 mmol) were added and the suspension was heated in a microwave oven at 100° C. for 20 minutes. The suspension was filtered and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/CH2Cl2 1:9 as the eluent. This afforded the title compound. 1H NMR (CDCl3) δ 7.36 (d, 1H), 7.22 (dd, 1H), 7.17 (d, 1H), 7.10 (d, 1H), 7.06-6.89 (m, 3H), 6.83 (dd, 1H), 6.79 (d, 1H), 5.88 (bs, 1H), 4.04 (t, 2H), 3.82 (t, 2H), 2.47 (s, 3H), 2.25 (s, 3H), 1.99 (m, 2H)

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-79b256cf666d4272b75e6da612969cb1
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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