Chlorosulfonyl isocyanate → HCID 71284559, compound

HRID 1481755Notes

Reaction equation

HRID 1481755 reaction equation
[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[CH:22]3)[C:16]([CH2:29][CH3:30])=[C:15]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:43]=[C:44]=O)(=O)=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[C:22]3[C:44]#[N:43])[C:16]([CH2:29][CH3:30])=[C:15]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 71285040HCID 71285040, compound

Product 1

HCID 71284559HCID 71284559, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2,4-bis(benzyloxy)-5-ethyl-6-(1-methyl-1H-indol-5-yl)nicotinate (880 mg, 1.74 mmol) in DMF (10 mL) was added chlorosulfonyl isocyanate (0.18 mL, 2.07 mmol, 1.2 eq) at 0° C. The reaction was monitored by LC-MS and starting material was completely consumed within 5 min. The reaction was quenched with water then extracted by CH2Cl2 (3×30 mL). The combined organic layers were dried over Na2SO4 and then concentrated to give a crude product which was purified by trituration with hexanes and CH2Cl2 to afford the title compound (732 mg, 79%).

Workup

  1. customwas completely consumed within 5 min
  2. customThe reaction was quenched with water
  3. extractionthen extracted by CH2Cl2 (3×30 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customto give a crude product which
  7. customwas purified by trituration with hexanes and CH2Cl2

Sources & evidence

ORD record
ord-b9d14d0e03ec46458a5b40bd9137e434
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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