Triethyl phosphite → HCID 59843340, compound

HRID 552314Notes

Reaction equation

HRID 552314 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH3:27])=[CH:16][C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25]I)[CH2:20][CH2:19]4)=[C:12]3[C:11]([CH3:28])=[CH:10]2)=[C:4]([CH3:29])[CH:3]=1.[P:30]([O:37]CC)([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33]>>[CH2:32]([O:31][P:30]([CH2:25][CH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:17]2[CH:16]=[C:15]([CH3:27])[N:14]=[C:13]3[N:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=4[CH3:29])[CH:10]=[C:11]([CH3:28])[C:12]=23)[CH2:19][CH2:20]1)(=[O:37])[O:34][CH2:35][CH3:36])[CH3:33]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 58281259HCID 58281259, compound

Product 1

HCID 59843340HCID 59843340, compound

Conditions

Temperature
160 °C

Procedure

Under N2 atmosphere, a mixture of 1-(4-bromo-2,6-dimethyl-phenyl)-4-[4-(2-iodo-ethyl)-piperidin-1-yl]-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridine (0.25 g) and triethyl phosphite (10 mL) was heated at 160° C. for 4.5 hours. After the reaction was completed, excess triethyl phosphate was removed under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=1/1) to obtain a colorless oil. The oily product was crystallized from diisopropylether (10 mL) to provide (2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethyl)-phosphonic acid diethyl ester (0.16 g) as a white crystal.

Workup

  1. customexcess triethyl phosphate was removed under reduced pressure
  2. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=1/1)
  3. customto obtain a colorless oil
  4. customThe oily product was crystallized from diisopropylether (10 mL)

Sources & evidence

ORD record
ord-da6bff7d33004a4cba6585e2e4baea47
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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