Aluminium lithium hydride → HCID 59394546, compound

HRID 1971399Notes

Reaction equation

HRID 1971399 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:28][N:29]=[N+]=[N-])[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:28][NH2:29])[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59394483HCID 59394483, compound

Product 1

HCID 59394546HCID 59394546, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Azidomethyl-pyridin-4-yloxy)-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide (165 mg, 0.36 mmol) is dissolved in THF (5 mL) at 0° C. and lithium aluminum hydride (0.55 mL, 0.55 mmol, 1.0M THF solution) is added. After 2 h, the mixture is quenched with water before extraction with EtOAc. The organic layer is washed with saturated aqueous NH4Cl and then dried over anhydrous Na2SO4. Following concentration the residue is separated via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH) to give the title compound. MS (ESI) m/z 427.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.29-8.39 (m, 2 H), 8.15 (d, J=3.8 Hz, 1 H), 8.09 (s, 1 H), 7.97 (d, J=8.1 Hz, 1 H), 7.64 (t, J=8.0 Hz, 1 H), 7.50 (d, J=7.6 Hz, 1 H), 7.45 (d, J=2.5 Hz, 1 H), 7.12 (dd, J=8.8, 2.5 Hz, 1 H), 7.00 (s, 1 H), 6.81 (d, J=3.3 Hz, 1 H), 6.76 (d, J=3.5 Hz, 1 H), 3.76 (s, 2 H).

Workup

  1. customthe mixture is quenched with water before extraction with EtOAc
  2. washThe organic layer is washed with saturated aqueous NH4Cl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentration the residue
  5. customis separated via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH)

Sources & evidence

ORD record
ord-2f200d9378e24acb9312764f56f15d07
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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