HCID 10702137, compound → HCID 10286804, compound

HRID 2105583Notes

Reaction equation

HRID 2105583 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]2.N[C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)N[C:18]([C:23]([O:25]CC)=O)=[CH:17]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:4]([C:22]1[CH:14]=[CH:15][C:16](/[CH:17]=[CH:18]/[C:23]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]3)=[O:25])=[CH:20][CH:21]=1)([CH3:8])([CH3:5])[CH3:3]

Participants

4

Reactant 3

HCID 10702137HCID 10702137, compoundHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10286804HCID 10286804, compound

Conditions

Temperature
25 °C

Procedure

(5-Aminoindol-2-yl)methan-1-ol. Ethyl 5-aminoindole-2-carboxylate, Example 74(a), (1.5 g, 7.3 mmol) was transferred to a round-bottomed flask and treated with lithium aluminum hydride (10 mL, 10 mmol, 1.0 M in THF, Aldrich) under N2. The reaction mixture was magnetically stirred at 25° C. for 1 h, then quenched by the dropwise addition of H2O (0.5 mL) followed by 20% aq. KOH (30 mL). The suspension was filtered and the aqueous phase extracted with EtOAc. The organic extract was concentrated in vacuo. Purification of the crude product by silica gel chromatography (20:80 hexane:EtOAc) provided the title product. MS (ESI, pos. ion) m/z: 163 (M+1).

Workup

  1. customquenched by the dropwise addition of H2O (0.5 mL)
  2. filtrationThe suspension was filtered
  3. extractionthe aqueous phase extracted with EtOAc
  4. extractionThe organic extract
  5. concentrationwas concentrated in vacuo
  6. customPurification of the crude product by silica gel chromatography (20:80 hexane:EtOAc)

Sources & evidence

ORD record
ord-b80a0b459a424ded96f7965da2ce9ce7
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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