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1-Bromo-2-methylpropane → HCID 57432096, compound

HRID 1406577
Notes
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Reaction equation

HRID 1406577 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[I:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([OH:22])=[O:21])[N:12]=[CH:11]2.Br[CH2:27][CH:28]([CH3:30])[CH3:29]>CN1C(=O)CCC1>[I:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([O:22][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:21])[N:12]=[CH:11]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropane2×HCID 10340Sodium CarbonateHCID 574320973-(5-iodo-1H-indazol-1-yl)benzoic acid

Product 1

HCID 57432096HCID 57432096, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
55 °C

Procedure

A 50 mL.s flask was charged with sodium carbonate (0.700 g, 6.60 mmol), 3-(5-iodo-1H-indazol-1-yl)benzoic acid (I1a) (2.185 g, 6 mmol) and NMP (15 mL) at 40° C. with magnetic stirring. After a couple of minutes 1-bromo-2-methylpropane (0.971 mL, 9.00 mmol) was added in one portion. After one hour at 40° C., the temperature was raised to 55° C. and another portion of 1-bromo-2-methylpropane (0.971 mL, 9.00 mmol) was added. The stirring was continued overnight. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed twice with water, dried over Na2SO4, filtered and evaporated to dryness to afford the title compound as a syrup (2.5 g, 99%). The product solidified to a beige material upon standing.

Workup

  1. waitThe stirring was continued overnight
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between water and ethyl acetate
  4. washThe organic phase was washed twice with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f878b1bd41e443ac9feeebf4cd652550
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916600B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes