Tetrabutylammonium Hydroxide → methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 1394889Notes

Reaction equation

HRID 1394889 reaction equation
[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.C1([C:25]2[C:26]3[CH:27]=[CH:28][C:29]([C:49]([O:51][CH3:52])=[O:50])=[CH:30][C:31]=3[N:32]3[CH2:38][C:37](C(OC)=O)=[CH:36][C:35]4[CH:43]=[C:44](OC)[CH:45]=[CH:46][C:34]=4[C:33]=23)CCCCC1>C1COCC1>[CH:46]1[C:34]2[C:33]3=[CH:25][C:26]4[CH:27]=[CH:28][C:29]([C:49]([O:51][CH3:52])=[O:50])=[CH:30][C:31]=4[N:32]3[CH2:38][CH:37]=[CH:36][C:35]=2[CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 58765200dimethyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate

Product 1

HCID 68832135methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetrabutylammonium hydroxide (1M in MeOH, 2.2 mL, 2.2 mmol) was added to a stirring solution of dimethyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate (1.0 g, 2.2 mmol) in THF (75 mL) and stirred at rt overnight. The reaction mixture was concentrated to 30 mL, diluted with EtOAc (120 mL), washed with 0.5 M HCl (aq.) (2×50 mL) and brine (40 mL), dried (MgSO4), filtered and concentrated to dryness to yield methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate, 13-cyclohexyl, 3-methoxy, 6-carboxylic acid (1.0 g, 2.2 mmol, quant.) as a yellow solid which was used without further purification. LCMS: m/e 446 (M+H)+, ret time 1.54 min, column A, 2 minute gradient.

Workup

  1. concentrationThe reaction mixture was concentrated to 30 mL
  2. additiondiluted with EtOAc (120 mL)
  3. washwashed with 0.5 M HCl (aq.) (2×50 mL) and brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2fc3b7ef5e3840c4ae4ecfc2b95c1cdd
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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