Methanol → HCID 90036239, compound

HRID 925642Notes

Reaction equation

HRID 925642 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]#[N:14])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH:11]=[O:12])=[CH:7]2.[C-]#N.[Na+].[CH3:18][OH:19]>[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([C:13]#[N:14])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:19][CH3:18])=[O:12])=[CH:7]2

Participants

5

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 90036793HCID 90036793, compound

Product 1

HCID 90036239HCID 90036239, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

To a stirred solution of 7-bromo-2-formyl-1H-indole-5-carbonitrile (0.17 g, 683 μmol) in MeOH (6.03 ml) was added sodium cyanide (167 mg, 3.41 mmol) and manganese dioxide (297 mg, 3.41 mmol) and the reaction mixture was allowed to stir for 17 h at room temperature. The mixture was evaporated, water (20 ml) was added and the mixture was extracted with ethyl acetate (2×15 ml). The combined organic layers were washed with brine, dried (MgSO4) and evaporated. The crude product (0.11 g) was further purified by flash chromatography on silica gel (heptane/ethyl acetate 0-20%) to yield methyl 7-bromo-5-cyano-1H-indole-2-carboxylate (0.105 g, 55%) as an orange solid, MS (ISN) m/z=279.3 [(M−H)+], mp 248° C.

Workup

  1. customThe mixture was evaporated
  2. additionwater (20 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate (2×15 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product (0.11 g) was further purified by flash chromatography on silica gel (heptane/ethyl acetate 0-20%)

Sources & evidence

ORD record
ord-311786e30e284ab8953a5780fde79586
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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