Water → HCID 87544567, compound

HRID 222100Notes

Reaction equation

HRID 222100 reaction equation
[C:1]([N:20]1[CH:28]=[C:27]2[C:22]([CH2:23][CH2:24][CH2:25][C:26]2=[N:29][OH:30])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=C[CH:32]=1.C[C:38]#[C:39][C:40]([O-:42])=[O:41].O>CS(C)=O>[CH3:32][O:42][C:40](=[O:41])[CH:39]=[CH:38][O:30]/[N:29]=[C:26]1/[C:27]2[C:22]([CH2:23][CH2:24][CH2:25]/1)=[N:21][N:20]([C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:28]=2

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6994510HCID 6994510, compoundHCID 86640247HCID 86640247, compound

Product 1

HCID 87544567HCID 87544567, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-trityl-2,5,6,7-tetrahydro-indazol-4-one oxime 3B (0.51 mmol) in dry DMSO (1 mL) and a catalytic amount of pyridine, methylpropiolate (1.1 eq) was added and the reaction mixture was stirred at rt for 1.5 h. The mixture was poured into water and the slurry was extracted with AcOEt. The organic layer was washed with brine, dried (Na2SO4) and concentrated to yield the title compound (94%). ESI (+) MS: m/z 478 (MH+). 1H NMR: 1.73-1.93 (m, 2H), 2.10-2.28 (m, 2H), 2.52-2.60 (m, 1H), 2.71-2.79 (m, 1H), 3.83 (s, 3H), 5.40 (d, J=12, 1H), 7.03 (s, 1H), 7.20-7.31 (m, 15H), 8.50 (d, J=12, 1H).

Workup

  1. extractionthe slurry was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a57124727d5d48d69f947e771c377267
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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