Potassium tert-butoxide → HCID 74890582, compound

HRID 475273Notes

Reaction equation

HRID 475273 reaction equation
[NH2:1][C:2]1[C:9]([C:10]#[CH:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:12])[CH:3]=1.CC([O-])(C)C.[K+]>C1COCC1>[Cl:12][C:4]1[CH:3]=[C:2]2[C:9]([CH:10]=[CH:11][NH:1]2)=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 866947484-Amino-2-chloro-5-ethynylbenzonitrile

Product 1

HCID 74890582HCID 74890582, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 240 (50 mg, 0.284 mmol) in THF (100 mL) was added t-BuOK (160 mg, 1.42 mmol). The mixture was heated at 75° C. for 3 h during which the color of the reaction mixture changed from yellow to brown. After the mixture was cooled, it was partitioned between EtOAc (200 mL) and H2O (50 mL). The organic layer was separated, washed with brine, dried and concentrated in vacuo to afford 43 mg (86%) of 6-chloro-1H-indole-5-carbonitrile (242) as white solid: 1H NMR (500 MHz, DMSO-d6) (511.80 (s, 1H), 8.21 (s, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 6.61 (d, 1H); MS (ESI) m/z=177.0 [M+1]+.

Workup

  1. temperatureAfter the mixture was cooled
  2. customit was partitioned between EtOAc (200 mL) and H2O (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3667633bd8364d6cb417c7ede19dd692
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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