Diisobutylaluminum hydride → HCID 69026650, compound

HRID 1432869Notes

Reaction equation

HRID 1432869 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([Cl:24])=[CH:10][N:11]2[S:14]([C:17]2[CH:22]=[CH:21][C:20](C)=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:7][CH:6]=1)=O.[CH3:25]C(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Cl:24][C:9]1[C:8]2[C:12](=[CH:13][C:5]([CH2:3][OH:2])=[CH:6][CH:7]=2)[N:11]([S:14]([C:17]2([CH3:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH2:18]2)(=[O:15])=[O:16])[CH:10]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54058252HCID 54058252, compound

Product 1

HCID 69026650HCID 69026650, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-chloro-1-(toluene-4-sulfonyl)-1H-Indole-6-carboxylic acid methyl ester (3.10 g, 8.53 mmol) in 50 mL of toluene at −78° C. is added DIBAL (13.8 mL of a 1.5M solution in toluene, 20.8 mmol) dropwise. The mixture is stirred at −78° C. for 2 h, then warmed to room temperature and stirred for 2 hours. The reaction mixture is quenched by the addition of MeOH and washed with saturated disodium tartrate solution. The aqueuos layer is extracted with Et2O. The combined organics are washed with saturated disodium tartrate solution, water and saturated NaCl solution. The organic phase is then dried over anhydrous MgSO4, filtered and concentrated to give the title compound (2.88 g). The crude product is used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ8.01 (s, 1H), 7.79 (d, 2H), 7.56 (s, 1H), 7.53 (d, 1H), 7.31 (d, 1H), 7.25 (d, 2H), 4.84 (s, 2H), 2.37 (s, 3H), 1.88 (bs, 1H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 2 hours
  3. customThe reaction mixture is quenched by the addition of MeOH
  4. washwashed with saturated disodium tartrate solution
  5. extractionThe aqueuos layer is extracted with Et2O
  6. washThe combined organics are washed with saturated disodium tartrate solution, water and saturated NaCl solution
  7. dry with materialThe organic phase is then dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a803a03b033a4fc3ab7a22e8f0fd170d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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