tert-Butyl acetate → HCID 91478440, compound

HRID 1818632Notes

Reaction equation

HRID 1818632 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH3:12].[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]([C:36](OCC)=[O:37])=[CH:23]2>C1COCC1>[CH2:29]([N:25]1[C:26]2[C:22](=[CH:21][C:20]([Cl:19])=[CH:28][CH:27]=2)[CH:23]=[C:24]1[C:36](=[O:37])[CH2:12][C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 10908tert-Butyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 13295699Ethyl 1-benzyl-5-chloro-1H-indole-2-carboxylate

Product 1

HCID 91478440HCID 91478440, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of LHMDS (38 mL, 1.0 M in THF, 38 mmol) was added tert-butyl acetate (5.2 mL, 38.3 mmol). After 30 min, a solution of the title compound of Example 12 Step A (4.00 g, 12.8 mmol) in THF (10 mL) was added, and the mixture was held at −78° C. for 50 min, whereupon it was placed in a 0° C. bath. After 2 h, the reaction mixture was quenched by addition of sat. aq. NH4Cl, and the aqueous phase was extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20%, then 20-100% EtOAc in hexanes) provided the title compound: LCMS B, tr=2.70 min, m/z 328.1 [M−tBu+H]+; 1H NMR (500 MHz, CDCl3) δ 7.70 (s, 1H), 7.31 (s, 1H), 7.29-7.18 (m, 5H), 7.02 (d, J=7.0 Hz, 2H), 5.84 (s, 2H), 3.86 (s, 2H), 1.40 (s, 9H).

Workup

  1. waitthe mixture was held at −78° C. for 50 min, whereupon it
  2. customwas placed in a 0° C.
  3. waitAfter 2 h
  4. customthe reaction mixture was quenched by addition of sat. aq. NH4Cl
  5. extractionthe aqueous phase was extracted with EtOAc
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (0 to 20%

Sources & evidence

ORD record
ord-a2acdc97886144aabd15a941622e6f76
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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