Dimethyl Sulfoxide → HCID 67044556, compound

HRID 2367102Notes

Reaction equation

HRID 2367102 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[OH:18][CH:19]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[N:32]=[CH:31]2)[C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23]>ClCCl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:43][CH:41]([Si:37]([CH:44]([CH3:46])[CH3:45])([CH:38]([CH3:40])[CH3:39])[N:33]1[C:34]2[C:30](=[CH:29][C:28]([C:19]([C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[C:22]#[N:23])=[O:18])=[CH:36][CH:35]=2)[CH:31]=[N:32]1)[CH3:42]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67044515HCID 67044515, compound

Product 1

HCID 67044556HCID 67044556, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of dimethylsulfoxide (71 μL, 1.0 mmol) in dichloromethane (1.5 mL) was cooled to −60° C. Addition of oxalyl chloride (44 μL, 0.50 mmol) was followed by addition of triethylamine (0.29 mL, 2.1 mmol) and 2-(hydroxy{1-[tris(1-methylethyl)silyl]-1H-indazol-5-yl}methyl)benzonitrile (0.17 g, 0.42 mmol in 2.0 mL of dichloromethane). The solution was allowed to warm to room temperature then diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted (2×100 mL ethyl acetate). The combined organic layers were dried (sodium sulfate), filtered and concentrated in vacuo. Column chromatography (silica gel, 5:1 hexanes/ethyl acetate) gave 0.070 g (42%) of 2-({1-[tris(1-methylethyl)silyl]-1H-indazol-5-yl}carbonyl)benzonitrile. 1H NMR (400 MHz, CDCl3): 8.32 (d, 1H), 8.13 (m, 1H), 8.01 (dd, 1H), 7.87 (m, 1H), 7.68 (m, 5H), 1.81 (m, 3H), 1.13 (d, 18H); MS (EI) for C24H29N3OSi: 248 (M−Si(iPr)3).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted (2×100 mL ethyl acetate)
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b24716085e984bf79b9981b18bfee4dd
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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