Sodium Sulfite → Benzyl (S)-2-(7-bromo-6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

HRID 1247006

Reaction equation

HRID 1247006 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C@@H:11]([CH3:23])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[Br:25][C:20]1[C:19]([OH:22])=[CH:18][CH:17]=[C:16]2[C:21]=1[N:13]([CH2:12][C@@H:11]([NH:10][C:9](=[O:24])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:23])[N:14]=[CH:15]2

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 135487328Benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

Product 1

HCID 136207273Benzyl (S)-2-(7-bromo-6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate (3.00 g, 9.23 mmol) from Step A in tetrahydrofuran (30 mL) was cooled in an ice bath, small portions of N-bromosuccinimide (1.64 g, 9.23 mmol) were added and the mixture was stirred for a few minutes followed by the addition of a saturated aqueous solution of sodium sulfite (150 mL). The mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were dried over magnesium sulfate, filtered, and evaporated to a white solid (3.76 g): mp 40° C.; LC/MS m/z 404/406.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to a white solid (3.76 g)

Sources & evidence

ORD record
ord-96449b0cdb6144c5a444c2498fa9eb97
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Linked notes

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