tert-Butanol → HCID 11630600, compound

HRID 907095Notes

Reaction equation

HRID 907095 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8](C(O)=O)=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[CH:4]=1)#[N:2].CC[N:19]([CH2:22]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>CCOC(C)=O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([NH:19][C:22](=[O:31])[O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 6386tert-Butanol2×HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59425917HCID 59425917, compound

Product 1

HCID 11630600HCID 11630600, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-cyano-1-ethyl-1H-indole-6-carboxylic acid (0.60 g, 2.80 mmol) from Example 1E, step A, in t-butanol (20 mL) was treated with Et3N (0.46 mL, 3.36 mmol) and diphenylphosphoryl azide (0.73 mL, 3.36 mmol) and then heated at reflux for 4 h. After cooling to room temperature, most of the t-butanol was removed in vacuo to give an oil, which was then dissolved in EtOAc. After washing with H2O, the organic phase was back-extracted with EtOAc and the organic layers were combined and washed sequentially with additional H2O, saturated NaHCO3 and saturated NaCl. The organic phase was dried, concentrated and the resulting crude product was purified by chromatography over silica gel using EtOAc/CH2Cl2 (0-1%) to afford 0.52 g (65%) of t-butyl (3-cyano-1-ethyl-1H-indol-6-yl)-carbamate as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. customwas removed in vacuo
  4. customto give an oil, which
  5. washAfter washing with H2O
  6. extractionthe organic phase was back-extracted with EtOAc
  7. washwashed sequentially with additional H2O, saturated NaHCO3 and saturated NaCl
  8. customThe organic phase was dried
  9. concentrationconcentrated
  10. customthe resulting crude product was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-5e37c16365054eb18922b8988f78815c
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…