Dimethyl Sulfoxide → 3-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehyde

HRID 2210559Notes

Reaction equation

HRID 2210559 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([CH3:50])([S:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH:22]=2)[N:17]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[C:16]=1[CH2:44][C:45]([CH3:49])([CH3:48])[CH2:46][OH:47])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:13][C:12]([CH3:50])([S:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH:22]=2)[N:17]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[C:16]=1[CH2:44][C:45]([CH3:49])([CH3:48])[CH:46]=[O:47])[CH3:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 193790463-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropanol

Product 1

HCID 193790433-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehydeYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (461 mg, 3.6 mmol) in CH2Cl2 (10 mls) at -78° C. was added dimethylsulfoxide (600 mg, 7.68 mmol) dropwise and the resulting mixture was stirred for 5 mins. A solution of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2yl]-2,2-dimethylpropanol (1.81 g, 3.2 mmol) in CH2Cl2 (5 mls) was then added dropwise and the reaction was stirred for 20 mins at -78° C. Triethylamine (1,62 g, 16.0 mmol) was then added dropwise, the cooling bath was withdrawn and the reaction allowed to warm to r.t. It was then diluted with aqueous sat'd NaHCO3 (20 mls) and the layers were separated. The aqueous was extracted with CH2Cl2 (2×20 mls). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 1:1) to afford 1.58 g (86%) of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehyde as a lemon yellow solid.

Workup

  1. stirringthe reaction was stirred for 20 mins at -78° C
  2. customthe cooling bath was withdrawn
  3. additionIt was then diluted with aqueous sat'd NaHCO3 (20 mls)
  4. customthe layers were separated
  5. extractionThe aqueous was extracted with CH2Cl2 (2×20 mls)
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 1:1)

Sources & evidence

ORD record
ord-7d7e3d7d869e4301969a7452469ed675
Source dataset
uspto-grants-1995_10
Patent number
US05459150

Reaction notes

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