4-Toluenesulfonyl chloride → HCID 89423033, compound

HRID 1481753Notes

Reaction equation

HRID 1481753 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH3:44])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19]1[N:24]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=3[O:34][CH3:35])[C:23](=[O:36])[C:22]([C:37]([O:39][CH3:40])=[O:38])=[C:21]([OH:41])[C:20]=1[CH2:42][CH3:43])=[CH:14][CH:13]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.[S:52](Cl)([C:55]1[CH:61]=[CH:60][C:58]([CH3:59])=[CH:57][CH:56]=1)(=[O:54])=[O:53]>C(Cl)Cl>[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH3:44])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19]1[N:24]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=3[O:34][CH3:35])[C:23](=[O:36])[C:22]([C:37]([O:39][CH3:40])=[O:38])=[C:21]([O:41][S:52]([C:55]3[CH:61]=[CH:60][C:58]([CH3:59])=[CH:57][CH:56]=3)(=[O:54])=[O:53])[C:20]=1[CH2:42][CH3:43])=[CH:14][CH:13]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 71284154HCID 71284154, compound

Product 1

HCID 89423033HCID 89423033, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 6-(2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indol-5-yl)-1-(2,4-dimethoxybenzyl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate (2.0 g, 3.2 mmol), prepared according to procedure described in Example 164, Step 2, in CH2Cl2 (15 mL) was added Et3N (0.68 mL, 4.9 mmol, 1.5 eq) and TsCl (0.74 g, 3.9 mmol, 1.2 eq) at 0° C. The mixture was allowed to warm to room temperature then stirred for 2 h. The solvent was removed and the residue was purified by flash column chromatography (0-25% EtOAc in CH2Cl2) to give the title compound (2.12 g, 85%). LC-MS 775.3 [M+H]+, RT 1.80 min.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash column chromatography (0-25% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-b3a3ca662f3c49febb3946b38e68d5e8
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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