Dimethyl Sulfoxide → HCID 10582514, compound

HRID 1439919Notes

Reaction equation

HRID 1439919 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[C:21]([CH2:24][CH2:25][CH2:26][OH:27])[CH:20]=[C:19]([Cl:28])[CH:18]=2)=[O:14].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][C:13]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[C:21]([CH2:24][CH2:25][CH:26]=[O:27])[CH:20]=[C:19]([Cl:28])[CH:18]=2)=[O:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53741601HCID 53741601, compound

Product 1

HCID 10582514HCID 10582514, compoundYield 112.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethyl sulfoxide (3.5 mL, 49.3 mmol) in dichloromethane (150 mL) was added dropwise oxalyl chloride (4.3 mL, 49.3 mmol) at -78° C. and the mixture was stirred for 20 rain at the same temperature. To the mixture was added dropwise a solution of 6-chloro-4-(3-hydroxypropyl)indole-2-carboxylic acid methyl ester (11.0 g, 41.1 mmol) in dichloromethane (1350 mL) at -78° C. over a period of 2 h. The mixture was stirred for 1 h at -78° C. and triethylamine (17.2 mL, 123.3 mmol) was added slowly at the same temperature. The mixture was allowed to warm at room temperature, diluted with water, and the organic layer was separated. The layer was washed with water, dried over MgSO4, and concentrated to give 12.24 g of the title compound (quant): 1H NMR (CDCl3) δ9.86 (t, 1H, J=1.0 Hz), 9.06 (bs, 1H), 7.29 (d, 1H, J=1.3 Hz), 7.22 (d, 1H, J=1.7 Hz), 6.96 (d, 1H, J=1.7 Hz), 3.96 (s, 3H), 3.20 (t, 2H, J=7.4 Hz), 2.90 (t, 2H, J=7.4 Hz).

Workup

  1. stirringThe mixture was stirred for 1 h at -78° C.
  2. customthe organic layer was separated
  3. washThe layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-01618d7314af4220a197e9f1d2bd1f8a
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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