N-bromobutanimide → HCID 136335135, compound

HRID 1247014Notes

Reaction equation

HRID 1247014 reaction equation
[OH:1][C@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1.[Br:15]N1C(=O)CCC1=O>O1CCCC1>[Br:15][C:11]1[C:10]([OH:13])=[CH:9][CH:8]=[C:7]2[C:12]=1[N:4]([CH2:3][C@H:2]([OH:1])[CH3:14])[N:5]=[CH:6]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 136335134HCID 136335134, compound

Product 1

HCID 136335135HCID 136335135, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[(R)-2-hydroxypropyl]-1H-indazol-6-ol (4.76 g, 24.8 mmol) in tetrahydrofuran (50 mL), cooled in an ice bath, added small portions of N-bromosuccinimide (4.41 g, 24.8 mmol) and stirred while the reaction warmed to room temperature. The reaction was quenched with aqueous saturated sodium sulfite (100 mL) and extracted with ethyl acetate (100 mL). The combined extracts were dried (magnesium sulfate), filtered and evaporated to a yellow solid (7 g): mp 134–136° C.; LC/MS m/z 271/273.

Workup

  1. customThe reaction was quenched with aqueous saturated sodium sulfite (100 mL)
  2. extractionextracted with ethyl acetate (100 mL)
  3. dry with materialThe combined extracts were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated to a yellow solid (7 g)

Sources & evidence

ORD record
ord-31d6d2861bf14a32bce8af7228e45576
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Reaction notes

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