Dichloromethane → HCID 22396774, compound

HRID 1071040Notes

Reaction equation

HRID 1071040 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].O[CH2:11][CH2:12][CH2:13][C:14]1[C:15]2[C:16]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23][C:17]=3[NH:18][C:19]=2[CH:20]=[CH:21][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:66]CCl>O1CCCC1.CO>[ClH:66].[CH2:27]1[C:16]2[C:15]3[C:14]([CH2:13][CH2:12][CH2:11][O:9][C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)=[CH:22][CH:21]=[CH:20][C:19]=3[NH:18][C:17]=2[CH2:23][CH2:24][NH:25][CH2:26]1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 5462977Diethyl azodicarboxylateHCID 22396655HCID 22396655, compound

Product 1

HCID 22396774HCID 22396774, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 25 mL scintillation vial containing a glass bead was added 4-cyanophenol (0.033 g, 0.277 mmol), a solution (0.250 M) of tert-butyl 10-(3-hydroxypropyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (1.0 mL, 0.250 mmol) in tetrahydrofuran, a solution (0.275 M) of triphenylphosphine (1.0 mL, 0.275 mmol) in tetrahydrofuran, and diethylazodicarboxylate (43.5 μL, 0.275 mmol). The vial was capped and orbitally shaken for 30 h. The mixture then was diluted with dichloromethane (1 mL) and methanol (1 mL). DOWEX® ion exchange resin (5.2 meq/gram, 0.5-0.75 g) was added and the mixtures were capped and shaken orbitally at 40° C. for 3 h. The mixture was filtered and the resin was washed (2× each) with dichloromethane, methanol, water, and tetrahydrofuran. The product then was eluted using a 4 N solution of ammonium hydroxide in methanol. Evaporation provided a residue which upon treatment with methanolic hydrochloric acid and evaporation led to the title compound. MS (EI) for m/z 346 (MH+).

Workup

  1. additionTo a 25 mL scintillation vial containing a glass bead
  2. customThe vial was capped
  3. additionwas added
  4. customthe mixtures were capped
  5. stirringshaken orbitally at 40° C. for 3 h
  6. filtrationThe mixture was filtered
  7. washthe resin was washed (2× each) with dichloromethane, methanol, water, and tetrahydrofuran
  8. washThe product then was eluted
  9. customEvaporation
  10. customprovided a residue which upon treatment
  11. customwith methanolic hydrochloric acid and evaporation

Sources & evidence

ORD record
ord-97087938d2fa415fae4ccf6fa0a13386
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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