Triphenylphosphine → HCID 66604478, compound

HRID 2410770Notes

Reaction equation

HRID 2410770 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[C:41]([C:53]([O:55][CH3:56])=[O:54])[C:42]3[NH:43][C:44]4[CH:45]=[C:46]([OH:52])[CH:47]=[CH:48][C:49]=4[C:50]=3[N:51]=2)=[CH:35][CH:34]=1.[O:57]1[CH2:62][CH2:61][N:60]([CH2:63][CH2:64][CH2:65]O)[CH2:59][CH2:58]1>C1COCC1>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[CH:40]=[C:41]([C:53]([O:55][CH3:56])=[O:54])[C:42]3[NH:43][C:44]4[CH:45]=[C:46]([O:52][CH2:65][CH2:64][CH2:63][N:60]5[CH2:61][CH2:62][O:57][CH2:58][CH2:59]5)[CH:47]=[CH:48][C:49]=4[C:50]=3[N:51]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1995763-Morpholino-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178497266HCID 178497266, compound

Product 1

HCID 66604478HCID 66604478, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (90 μL, 0.57 mmol) was added to a solution of triphenylphosphine (149 mg, 0.567 mmol), methyl 2-(4-chlorophenyl)-7-hydroxy-5H-pyrido[3,2-b]indole-4-carboxylate (100 mg, 0.283 mmol) and 3-morpholinopropan-1-ol (78 μL, 0.57 mmol) in dry THF (1.4 mL) at RT under nitrogen. After 1 hr, the reaction was quenched with a little water and the product was captured on an SCX cartridge, washed with MeOH and DCM, and then released with 2 N NH3 in MeOH. Radial chromatography (step gradient elution with DCM containing 0 to 1% MeOH) afforded impure methyl 2-(4-chlorophenyl)-7-(3-morpholinopropoxy)-5H-pyrido[3,2-b]indole-4-carboxylate (75 mg) as a yellow solid. MS (ESI) m/z 480.0 (M+H).

Workup

  1. customthe reaction was quenched with a little water
  2. washwashed with MeOH and DCM
  3. washRadial chromatography (step gradient elution with DCM containing 0 to 1% MeOH)

Sources & evidence

ORD record
ord-4994884c42c54bf99a6eb41046dc5227
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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