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

HRID 1406577Notes

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

Participants

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

waitThe stirring was continued overnight
temperatureAfter cooling
customthe reaction mixture was partitioned between water and ethyl acetate
washThe organic phase was washed twice with water
dry with materialdried over Na2SO4
filtrationfiltered
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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