N,N,N',N'-Tetramethylazodicarboxamide → 2-Methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423119Notes

Reaction equation

HRID 2423119 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:6][C:7]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[CH3:5].N(C(N(C)C)=O)=NC(N(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:5][N:4]1[CH2:6][C:7]2=[C:8]3[C:12](=[CH:13][CH:14]=[C:15]2[O:16][CH2:2][CH2:3]1)[NH:11][CH:10]=[CH:9]3

Participants

5

Reactant 3

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 11776TriphenylphosphineHCID 672405814-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-1H-indol-5-ol2×

Product 1

HCID 672416342-Methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indoleYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-1H-indol-5-ol (Intermediate 5, 0.44 g, 2.0 mmol), 1,1′-Azobis(N,N-dimethylformamide) (0.52 mg, 3.0 mmol) and triphenylphosphine (0.79 mg, 3.0 mmol) was dissolved in THF (10 mL) and stirred at room temperature overnight. The mixture was evaporated and the crude material was purified by flash chromatography on silica gel using a MeOH-ethylacetate gradient, 4-32% MeOH, to give 136 mg of the title compound. MS m/z 203 [M+H]+.

Workup

  1. customThe mixture was evaporated
  2. customthe crude material was purified by flash chromatography on silica gel using a MeOH-ethylacetate gradient, 4-32% MeOH

Sources & evidence

ORD record
ord-2fcacc383ab342588f9ff01b5cf2ba69
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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