tert-Butanol → HCID 11630600, compound

HRID 1009524Notes

Reaction equation

HRID 1009524 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) is 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 is removed in vacuo to give an oil, which is then dissolved in EtOAc. After washing with H2O, the organic phase is back-extracted with EtOAc and the organic layers are combined and washed sequentially with additional H2O, saturated NaHCO3 and saturated NaCl. The organic phase is dried, concentrated and the resulting crude product is 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. customis removed in vacuo
  4. customto give an oil, which
  5. washAfter washing with H2O
  6. extractionthe organic phase is back-extracted with EtOAc
  7. washwashed sequentially with additional H2O, saturated NaHCO3 and saturated NaCl
  8. customThe organic phase is dried
  9. concentrationconcentrated
  10. customthe resulting crude product is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-b055aaccaffb457d83c5bbd98c9a16cb
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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