Hydrochloric Acid → HCID 90036793, compound

HRID 925641Notes

Reaction equation

HRID 925641 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:18]#[N:19])=[CH:14][C:15]=2[Br:17])[CH:10]=[C:9]1[CH:20](OCC)[O:21]CC)=O)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[Br:17][C:15]1[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[C:11]2[C:16]=1[NH:8][C:9]([CH:20]=[O:21])=[CH:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 118341170HCID 118341170, compound

Product 1

HCID 90036793HCID 90036793, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-bromo-5-cyano-2-diethoxymethyl-indole-1-carboxylic acid tert-butyl ester (0.29 g, 685 μmol) was solved in THF (2 ml) and cooled to 0° C. Afterwards hydrochloric acid (37%, 1.35 g, 1.14 ml, 13.7 mmol) was added quickly, and the mixture was allowed to stir for 15 min at 0° C. and for 5 h at room temperature. The mixture was cooled (ice bath), saturated sodium carbonate solution (10 ml) was added and the mixture was extracted with ethyl acetate (2×25 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and evaporated. The crude product (0.18 g) was further purified by flash chromatography on silica gel (heptane/ethyl acetate 0-20%) to yield 7-bromo-2-formyl-1H-indole-5-carbonitrile (0.17 g, 100%) as an orange solid, MS (ISN) m/z=247.4 [(M−H)+], mp 117.5° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (2×25 ml)
  3. washThe combined organic layers were washed with brine (30 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product (0.18 g) was further purified by flash chromatography on silica gel (heptane/ethyl acetate 0-20%)

Sources & evidence

ORD record
ord-8dc40e5b250b4d68a03bc3b2efe7ce4d
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

Loading…